Pyrimidine or triazine derivatives and herbicides

ABSTRACT

A herbicide containing a pyrimidine or triazine derivative of the formula (I): ##STR1## [wherein A is a furan ring, a pyrimidine ring, a 1,2,4-triazine ring or the like which may suitably be substituted, R is a hydroxyl group or a lower alkoxy group, each of R 1  and R 2  which may be the same or different, is a halogen atom, a lower alkyl group or a lower alkoxy group, W is an oxygen atom or a sulfur atom, and Z is nitrogen or a methine group] and its salt, as an active ingredient, is presented. The pyrimidine or triazine derivative of the present invention has excellent herbicidal effects against noxious weeds in paddy fields, upland fields and non-agricultural fields.

TECHNICAL FIELD

This application is a 371 of PCT/JP 92/01690, filed on Dec. 14, 1992.

The present invention relates to herbicides which contain pyrimidine or triazine derivatives and their salts as active ingredients and which can be applied to paddy fields, upland fields and non-agricultural fields.

BACKGROUND ART

It has been already disclosed in Japanese Unexamined Patent Publication No. 121973/1990 that the following compounds have herbicidal activities: ##STR2##

However, the herbicidal effects off the compounds disclosed in this publication are not necessarily adequate. The present inventors have conducted extensive researches on pyrimidine or triazine compounds with an aim to develop further improved compounds and as a result, have found that pyrimidine or triazine derivatives of the present invention having a heterocyclic ring introduced exhibit excellent herbicidal effects not only against annual weeds but also against perennial weeds, and they are highly safe to crop plants. The present invention has been accomplished on the basis of this discovery.

DISCLOSURE OF THE INVENTION

The present invention provides a pyrimidine or triazine derivative of the formula (I): ##STR3## wherein A is a heterocyclic ring of the formula: ##STR4## R is a hydrogen atom, a hydroxyl group, an imidazolyl group, a C₁ -C₆ alkoxy group, a C₃ -C₆ alkenyloxy group, a C₃ -C₆ alkynyloxy group, a C₁ -C₆ alkylthio group, a C₃ -C₇ cycloalkoxy group, a benzyloxy group, a substituted benzyloxy group, a benzylthio group, a substituted benzylthio group, a C₃ -C₆ cycloalkylthio group, a C₁ -C₄ alkoxy C₁ -C₄ alkoxy group, a furyloxy group, a tetrahydrofuryloxy group, a phenoxy group, a substituted phenoxy group, a C₂ -C₄ aralkyloxy group, a C₁ -C₄ alkylthio C₁ -C₄ alkoxy group, a cyano C₁ -C₄ alkoxy group, a C₁ -C₄ alkoxycarbonyl C₁ -C₄ alkoxy group, an N,N-di C₁ -C₃ alkylamino C₁ -C₃ alkoxy group, an N,N-di C₁ -C₃ alkylamino C₁ -C₃ alkylthio group, a C₃ -C₉ linear or cyclic alkylidene aminoxy group, a C₁ -C₄ alkylsulfonylamino group, a phenylsulfonylamino group, a substituted phenylsulfonylamino group, a trimethylsilylethoxy group, a group of the formula --NR⁴ R⁵ (wherein each of R⁴ and R⁵ which may be the same or different, is a hydrogen atom, a hydroxyl group, a C₁ -C₆ alkyl group, a C₁ -C₆ alkoxy group, a C₃ -C₆ alkenyl group, a phenyl group, a substituted phenyl group, a C₃ -C₆ cycloalkyl group, a C₁ -C₃ alkoxy C₁ -C₃ alkyl group, a C₁ -C₃ acyl group, a C₃ -C₆ alkynyl group, a C₃ -C₅ alkenyloxy group, a C₃ -C₅ alkynyloxy group, a benzyloxy group, a substituted benzyloxy group, a C₁ -C₄ alkoxycarbonyl C₁ -C₃ alkyl group, a C₁ -C₄ alkoxycarbonyl C₁ -C₃ alkoxy group, an amino group, a dimethylamino group, a cyano group, a C₁ -C₄ alkylsulfonyl group, a phenylsulfonyl group, a substituted phenylsulfonyl group, an acetylamino group or an anilino group, or R⁴ and R⁵ may together form a ring which may contain a hetero atom), each of R¹ and R² which may be the same or different, is a hydrogen atom (provided that a case where R¹ and R² are the same, is excluded), a halogen atom, a C₁ -C₆ alkyl group, a C₁ -C₆ haloalkyl group, a C₁ -C₆ alkoxy group, a C₁ -C₆ haloalkoxy group, a C₁ -C₆ alkylthio group, a phenoxy group, a substituted phenoxy group, a C₁ -C₃ alkoxy C₁ -C₃ alkyl group, a C₃ -C₆ cycloalkyl group, a C₂ -C₅ alkenyl group, a C₃ -C₅ alkenyloxy group, a C₂ -C₄ alkynyl group, a C₃ -C₅ alkynyloxy group, a C₁ -C₃ alkylthio C₁ -C₃ alkyl group, a group of the formula --NR⁶ R⁷ (wherein each of R⁶ and R⁷ which may be the same or different, is a hydrogen atom, a hydroxyl group, a C₁ -C₄ alkyl group, a C₁ -C₄ alkoxy group, a C₂ -C₄ alkenyl group, a C₂ -C₄ alkynyl group, a C₃ -C₅ alkenyloxy group or a C₃ -C₅ alkynyloxy group, or R⁶ and R⁷ may together form a ring which may contain a hetero atom), R³ is a hydrogen atom, a halogen atom, a C₁ -C₆ alkyl group, a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a benzoyl group, a substituted benzoyl group, a C₁ -C₃ acyl group, C₁ -C₆ alkylsulfonyl group, a phenylsulfonyl group or a substituted phenylsulfonyl group, X is a hydrogen atom, a C₁ -C₆ alkyl group, a C₁ -C₆ haloalkyl group, a C₁ -C.sub. 6 alkoxy group, a C₁ -C₆ haloalkoxy group, a C₃ -C₆ alkenyl group, a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a phenoxy group, a substituted phenoxy group, a benzyloxy group, a substituted benzyloxy group, a C₁ -C₃ acyl group, a naphthyl group, a benzoyl group, a substituted benzoyl group, a halogen atom, a nitro group, a group of the formula --NR⁸ R⁹ (wherein each of R⁸ and R⁹ which may be the same or different, is a hydrogen atom, a C₁ -C₁₂ alkyl group, a C₃ -C₆ alkenyl group, a C₃ -C₆ alkynyl group, a phenyl group, a substituted phenyl group, a naphthyl group, a C₁ -C₃ acyl group, a benzoyl group or a substituted benzoyl group, or R⁸ and R⁹ may together form a ring which may contain a hetero atom), a C₁ -C₆ alkylthio group, a C₁ -C₆ alkylthio C₁ -C₃ alkyl group, a phenylthio group, a substituted phenylthio group, a C₁ -C₆ alkoxycarbonyl group, a carboxyl group, a cyano group, a carbamoyl group, a N--C₁ -C₆ alkylcarbamoyl group, a C₁ -C₆ alkylsulfonyl group, a phenylsulfonyl group, a substituted phenylsulfonyl group, a C₁ -C₆ alkoxy C₁ -C₆ alkyl group, a C₁ -C₆ alkoxy C₁ -C₆ alkoxy group, a C₁ -C₆ alkylthio C₁ -C₆ alkyl group, a C₁ -C₆ alkoxy C₁ -C₆ alkylthio group, a C₁ -C₆ alkylthio C₁ -C₆ alkoxy group, an allylthio group, a C₁ -C₆ alkylsulfinyl group, a furyl group, a thienyl group, a pyridyl group, a pyrimidinyloxy group which may be substituted, a pyrimidinylthio group which may be substituted, a substituted triazinyloxy group, a substituted triazinylthio group, W is an oxygen atom, a sulfur atom or a group of the formula --NR¹⁰ (wherein R¹⁰ is a hydrogen atom, a C₁ -C₃ alkyl group, a C₂ -C₅ alkenyl group, a C₂ -C₄ alkynyl group, a C₁ -C₃ alkoxy C₁ -C₃ alkyl group, a C₁ -C₃ alkylsulfonyl group, a phenylsulfonyl group, a substituted phenylsulfonyl group, a C₁ -C₃ acyl group, a benzoyl group or a substituted benzoyl group), Z is a nitrogen atom or a methine group, and n is an integer of from 1 to 5; and its salt; and a herbicide containing such a compound as an active ingredient.

Here, for R, the alkoxy group may, for example, be a methoxy group, an ethoxy group, an isopropoxy group, a propoxy group or a butoxy group, the alkenyloxy group may, for example, be an allyloxy group, the alkynyloxy group may, for example, be a propargyloxy group, the alkylthio group may, for example, be an ethylthio group or a propylthio group, the cycloalkoxy group may, for example, be a cyclopentyloxy group or a cyclohexyl group, the substituted benzyloxy group may, for example, be a benzyloxy group substituted by a chlorine atom, a methyl group or a methoxy group, the substituted benzylthio group may, for example, be a chlorine atom-substituted benzyloxy group, the cycloalkylthio group may, for example, be a cyclopentylthio group, the alkoxyalkoxy group may, for example, be a methoxymethoxy group, the substituted phenoxy group may, for example, be a phenoxy group substituted by a chlorine atom or a methyl group, the aralkyloxy group may, for example, be a phenethyloxy group, the alkylthioalkoxy group may, for example, be a methylthiomethoxy group, the cyanoalkoxy group may, for example, be a cyanomethoxy group, the alkoxycarbonylalkoxy group may, for example, be a methoxycarbonylmethoxy group or an ethoxycarbonylmethoxy group, the N,N-dialkylaminoalkoxy group may, for example, be an N,N-dimethylaminoethoxy group, the N,N-dialkylaminoalkylthio group may, for example, be an N,N-dimethylaminoethylthio group, the linear or cyclic alkylidene aminoxy group may, for example, be an isopropylideneaminoxy group, a 3-pentylideneaminoxy group, a 4-heptylideneaminoxy group, a cyclohexylideneaminoxy group, a cycloheptylideneaminoxy group or a 4-tetrahydropyranylideneaminoxy group, the alkylsulfonylamino group may, for example, be a methylsulfonylamino group or an ethylsulfonylamino group, and the substituted phenylsulfonylamino group may, for example, be a phenylsulfonylamino group substituted by e.g. a chlorine atom, a methyl group, a nitro group or a methoxycarbonyl group.

For R⁴ or R⁵ in the formula --NR⁴ R⁵, the alkyl group may, for example, be a methyl group, the alkoxy group may, for example, be a methoxy group or an ethoxy group, the substituted phenyl group may, for example, be a phenyl group substituted by e.g. a chlorine atom or a methyl group, the cycloalkyl group may, for example, be a cyclohexyl group, the alkoxyalkyl group may, for example, be a methoxymethyl group or a methoxyethyl group, the acyl group may, for example, be an acetyl group, the alkynyl group may, for example, be a propargyl group, the alkenyloxy group may, for example, be an allyloxy group, the alkynyloxy group may, for example, be a propargyloxy group, the substituted benzyloxy group may, for example be a chloro-substituted benzyloxy group, the alkoxycarbonylalkyl group may, for example, be a methoxycarbonylmethyl group, the alkoxycarbonylalkoxy group may, for example, be a methoxycarbonylmethoxy group, an ethoxycarbonylmethoxy group or a methoxycarbonylethoxy group, the alkylsulfonyl group may, for example, be a methylsulfonyl group or an ethylsulfonyl group, the alkylsulfonyl group may, for example, be a methylsulfonyl group or an ethylsulfonyl group, the substituted phenylsulfonyl group may, for example, be a phenylsulfonyl group substituted by e.g. a chlorine atom, a methoxycarbonyl group, a methyl group or a nitro group, and the ring which may contain a hetero atom, formed by R⁴ or R⁵, may, for example, be a piperidino group, a morpholino group or a pyrrolidino group.

For R¹ or R², the halogen atom may, for example, be a chlorine atom, the alkyl group may, for example, be a methyl group, the haloalkyl group may, for example, be a trifluoromethyl group, the alkoxy group may, for example, be a methoxy group, the haloalkoxy group may, for example, be a difluoromethoxy group, the alkylthio group may, for example, be a methylthio group, the cycloalkyl group may, for example, be a cyclopropyl group, the alkenyloxy group may, for example, be an allyloxy group, the alkynyl group may, for example, be a 1-propynyl group, the alkynyloxy group may, for example, be a 2-propionyloxy group, and the alkylthioalkyl group may, for example, be a methylthiomethyl group. The alkyl group for R⁶ or R⁷ of the formula --NR⁶ R⁷ may, for example be a methyl group.

For R³, the halogen atom may, for example, be a chlorine atom, the alkyl group may, for example, be a methyl group, the substituted phenyl group may, for example, be a phenyl group substituted by e.g. a chlorine atom or a methyl group, and the substituted benzyl group may, for example, be a benzyl group substituted by e.g. a chlorine atom or a methyl group.

For X, the alkyl group may, for example, be a methyl group, an isopropyl group or a t-butyl group, the haloalkyl group may, for example, be a perfluoroethyl group, the alkoxy group may, for example, be an ethoxy group or an isobutyloxy group, the alkenyl group may, for example, be a 1-propenyl group, the substituted phenyl group may, for example, be a phenyl group substituted by e.g. a chlorine atom, a methyl group or a trifluoromethyl group, the halogen atom may, for example, be a chlorine atom or a fluorine atom, the alkylthio group may, for example, be a methylthio group, the alkylthioalkyl group may, for example, be a methylthiomethyl group, the alkoxycarbonyl group may, for example, be an ethoxycarbonyl group, the alkylsulfonyl group may, for example, be a methylsulfonyl group, the pyridyl group may, for example, be a 3- or 4-pyridyl group, the pyrimidinyloxy group which may be substituted, may, for example, be a (4,6-dimethoxypyrimidin-2-yl)oxy group, and the pyrimidinylthio group which may be substituted, may, for example, be a (4,6-dimethoxypyrimidin-2-yl)thio group. For R⁸ or R⁹ in the formula --NR⁸ R⁹, the alkyl group may, for example, be a methyl group, an ethyl group or an isopropyl group, the substituted phenyl group may, for example, be a methyl-substituted phenyl group, and the substituted benzoyl group may, for example, be a chlorine atom-substituted benzoyl group.

For R¹⁰ in the formula --NR¹⁰ for W, the alkyl group may, for example, be a methyl group, the alkenyl group may, for example, be an allyl group, the alkoxyalkyl group may, for example, be a methoxymethyl group, the alkylsulfonyl group may, for example, be a methylsulfonyl group, and the acyl group may, for example, be a formyl group or an acetyl group.

Compounds of the present invention can be produced, for example, in accordance with the following processes A to H.

Process A ##STR5## (wherein A¹ is a heterocyclic ring of the formula: ##STR6## L is a halogen atom, an alkylsulfonyl group, a benzylsulfonyl group, a substituted benzylsulfonyl group, an alkylsulfonate group or a haloalkylsulfonate group, and W, X, Z, n, R, R¹, R² and R³ are as defined above.)

A compound of the formula (IV) can be produced by reacting a compound of the formula (II) with a compound of the formula (III) in a suitable solvent in the presence of an at least equimolar amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours. As the base, an alkali metal such as metal lithium, metal sodium or metal potassium, an organic lithium reagent such as n-butyl lithium or lithium diisopropylamine, an alkali metal hydride or an alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, an alkali metal alkoxide such as potassium t-butoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, may be used. As the solvent, a hydrocarbon solvent such as hexane, benzene, toluene or xylene, a halogenated hydrocarbon solvent such as dichloromethane or chloroform, an ether solvent such as diethyl ether, tetrahydrofuran or 1,4-dioxane, an ester solvent such as methyl acetate or ethyl acetate, a ketone solvent such as acetone or methyl ethyl ketone, an aprotic polar solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide, or other solvent such as acetonitrile, may be used.

Process B ##STR7## (wherein A² is a heterocyclic ring of the formula: ##STR8## L, W, X, Z, N, n, R, R¹, R² and R³ are as defined above.)

A compound of the formula (VII) can be produced by reacting a compound of the formula (V) with a compound of the formula (VI) in a suitable solvent in the presence of an at least equimolar amount of a base at a temperature within a range of from room temperature to the boiling point of the solvent for from 0.5 to 24 hours. The base and the solvent to be used, may be the same as those described for Process A.

Process C ##STR9## (wherein R¹¹ is a C₁ -C₆ alkyl group, a C₃ -C₇ cycloalkyl group, a benzyl group, a substituted benzyl group, a C₁ -C₄ alkoxy group C₁ -C₄ alkyl group, a tetrahydrofuryl group, a C₂ -C₄ aralkyl group, a C₁ -C₄ alkylthio C₁ -C₄ alkyl group, a cyano C₁ -C₄ alkyl group, a C₁ -C₄ alkoxycarbonyl C₁ -C₄ alkyl group, a N,N-di C₁ -C₃ alkylamino C₁ -C₃ alkyl group, and A, L, R¹, R², W and Z are as defined above.)

A compound of the formula (X) can be produced by reacting a compound of the formula (VIII) with a compound of the formula (IX) in a solvent in the presence of a base at a reaction temperature of from -10° to 200° C. for from 0.1 to 30 hours. Here, as the base, an organic or inorganic base such as potassium carbonate, sodium hydrogencarbonate, sodium hydride, triethylamine, pyridine or 4-dimethylaminopyridine, may be used. Further, as the solvent, acetone, acetonitrile, tetrahydrofuran, N,N-dimethylacetamide, dimethylsulfoxide, benzene, toluene, chlorobenzene, dichloromethane or chloroform may, for example, be used.

Process D ##STR10## (wherein each of R¹² and R¹³ which may be the same or different, is a C₁ -C₄ alkyl group, or they may form a ring which may contain a hetero atom, and A, W, Z, R¹ and R² are as defined above.)

A compound of the formula (XII) can be produced by reacting a compound of the formula (VIII) with a compound of the formula (XI) in a solvent in the presence of a base and a phosphoric acid dichloride such as dimethylamide phosphoryl dichloride or phenylphosphoro dichloride at a reaction temperature of from 10° to 100° C. for from 1 to 10 hours. Here, as the base, an organic tertiary amine such as pyridine or triethylamine, may, for example, be used. Further, as the solvent, N,N-dimethylformamide, N,N-dimethylacetamide or dimethylsulfoxide may, for example, be used.

Process E ##STR11## (wherein R¹⁴ is a C₁ -C₆ alkoxy group, a C₃ -C₆ alkenyloxy group, a C₃ -C₆ alkynyloxy group, a C₁ -C₆ alkylthio group, a C₃ -C₇ cycloalkoxy group, a benzyloxy group, a substituted benzyloxy group, a benzylthio group, a substituted benzylthio group, a C₃ -C₆ cycloalkylthio group, a C₁ -C₄ alkoxy C₁ -C₄ alkoxy group, a furyloxy group, a tetrahydrofuryloxy group, a phenoxy group, a substituted phenoxy group, a C₂ -C₄ aralkyloxy group, a C₁ -C₄ alkylthio C₁ -C₄ alkoxy group, a cyano C₁ -C₄ alkoxy group, a C₁ -C₄ alkoxycarbonyl C₁ -C₄ alkoxy group, a N,N-di C₁ -C₃ alkylamino C₁ -C₃ alkoxy group, a N,N-di C₁ -C₃ alkylamino C₁ -C₃ alkylthio group, a C3-C₉ linear or cyclic alkylidene aminoxy group, or a trimethylsilylethoxy group, A, R¹, R², Z and W are as defined above, and M is a monovalent cation.)

A compound of the formula (XIII) can be produced by reacting a compound of the formula (X) in a mixture system of water and a solvent in the presence of a base at a reaction temperature of from 0° to 120° for from 1 to 24 hours. Then, a compound of the formula (VIII) can be obtained by acidifying the compound of the formula (XIII) to pH 3 to 4 by e.g. hydrochloric acid in accordance with a conventional method. Here, as the base, an inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate may, for example, be used. Further, as the solvent, acetone, acetonitrile, methanol, ethanol, dioxane, tetrahydrofuran, dimethoxyethane, N,N-dimethylformamide, N,N,-dimethylacetamide or dimethylsulfoxide may, for example, be used. In a case where R¹² in the formula (X) is a benzyl group or a substituted benzyl group, a compound of the formula (VIII) can be obtained by a hydrogenating reaction under an ordinary pressure using e.g. palladium-carbon as a catalyst.

Process F

An organic or inorganic salt of a compound of the formula (XIII) can be produced by reacting a compound of the formula (VIII) with a base in a solvent such as water, an alcohol, acetonitrile, acetone, an ether, N,N-dimethylformamide or dimethylsulfoxide at a reaction temperature of from 0° to 100° C. for from 0.2 to 10 hours. Here, as the base, an alkali metal or an alkaline earth metal hydroxide such as sodium hydroxide, potassium hydroxide or calcium hydroxide, a carbonate such as sodium carbonate, potassium carbonate or calcium carbonate, ammonia, or a primary, secondary or tertiary amine such as ethylamine, dimethylamine, isopropylamine, diisopropylamine, diethanolamine or triethylamine, may be used.

Process G

A compound of the formula (VIII) and an equimolar amount of an aqueous sodium hydroxide solution are reacted at room temperature, then a metal halide such as magnesium chloride, copper chloride, calcium chloride, iron chloride, zinc chloride or manganese chloride and a sulfate such as magnesium sulfate, copper sulfate, calcium sulfate, iron sulfate, zinc sulfate or manganese sulfate are added, and the mixture is reacted in a solvent such as water or an alcohol at a temperature of from -10° C. to 200° C. for from one minute to 20 hours, whereby an inorganic salt of a compound of the formula (XIII) can be produced.

Process H ##STR12## (wherein R¹⁵ is a C₁ -C₄ alkyl group, a phenyl group or a substituted phenyl group, and R¹, R², W, Z and A are as defined above. )

A compound of the formula (XV) can be produced by reacting a compound of the formula (VIII) with a compound of the formula (XIV) in a solvent at a reaction temperature of from -10° to 100° C. for form 1 to 10 hours. As the solvent, ethyl ether, tetrahydrofuran, dioxane, benzene or toluene may, for example, be used. Then, a compound of the formula (XVII) can be produced by reacting a compound of the formula (XV) with a compound of the formula (XVI) in a solvent in the presence of a base at a reaction temperature of from -20° to 150° C. for from 0.5 to 20 hours. Here, as the base, sodium hydride, metal sodium, potassium t-butoxide, butyl lithium, potassium carbonate or sodium carbonate may, for example, be used. Further, as the solvent, acetone, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, benzene or toluene may, for example, be used.

Now, the processes for producing the compounds of the present invention, methods for preparation of formulations and methods for application will be specifically described with reference to Examples.

BEST MODE FOR CARRYING OUT THE INVENTION EXAMPLE 1 (Process A)

Preparation of ethyl 1-chloro-4-(4,6-dimethoxypyrimidin-2-yloxy)isoquinoline-3-carboxylate (Compound No. 754)

40 ml of N,N-dimethylformamide was added to 1.8 g (7.1 mmol) of ethyl 1-chloro-4-hydroxyisoquinoline-3-carboxylate, 1.4 g (8.6 mmol) of 4,6-dimethoxy-2-fluoropyrimidine and 1.2 g (8.6 mmol) of potassium carbonate, and the mixture was heated and stirred at from 80° to 100° C. for 3 hours. After cooling, the reaction solution was poured into water and washed with ethyl acetate. The aqueous layer was adjusted to pH 3 to 4 with a 10% HCl solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.6 g (yield: 21.4%) of the desired product. Refractive index: 1.5811.

EXAMPLE 2 (Process A)

Preparation of methyl 3-(4,6-dimethoxypyrimidin-2-yloxy)benzofuran-2-carboxylate (Compound No. 674)

100 ml of N,N-dimethylsulfoxide was added to 5.0 g (26.0 mmol) of methyl 3-hydroxybenzofuran-2-carboxylate, 4.6 g (28.9 mmol) of 4,6-dimethoxy-2-fluoropyrimidine and (43.4 mmol) of potassium carbonate, and the mixture was heated and stirred at from 80° to 100° C. for 30 minutes. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 3.6 g (yield: 41.9%) of the desired product. Melting Point: 135°-138° C.

EXAMPLE 3 (Process A)

Preparation of ethyl 4-(4,6-dimethoxypyrimidin-2-yloxy)-2-methylthiomethylthiophene-3-carboxylate (Compound No. 170)

50 ml of N,N-dimethylformamide was added to 3.5 g (15.1 mmol) of ethyl 4-hydroxy-2-methylthiomethylthiophene-3-carboxylate, 3.3 g (15.1 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 2.1 g (15.2 mmol) of potassium carbonate, and the mixture was heated and stirred at from 90° to 100° C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2.8 g (yield: 50.0%) of the desired product.

EXAMPLE 4 (Process B)

Preparation of methyl 3-(4,6-dimethoxypyrimidin-2-yloxy)pyrazine-2-carboxylate (Compound No. 622)

150 ml of N,N-dimethylformamide was added to 3.5 g (2.03 mmol) of methyl 3-chloropyrazine-2-carboxylate, 3.6 g (2.31 mmol) of 4,6-dimethoxy-2-hydroxypyrimidine and 4.2 g (3.04 mmol) of potassium carbonate, and the mixture was heated and stirred at 100° C. for 25 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.5 g (yield: 7.0%) of the desired product. Melting point: 88°-93° C.

EXAMPLE 5 (Process B)

Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yloxy)quinoxaline-2-carboxylate (Compound No. 762)

100 ml of N,N-dimethylformamide was added to 2.3 g (9.72 mmol) of ethyl 3-chloroquinoxaline-2-carboxylate, 2.0 g (12.8 mmol) of 4,6-dimethoxy-2-hydroxypyrimidine and 1.8 g (13.0 mmol) of potassium carbonate, and the mixture was heated and stirred at 100° C. for 23 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2.2 g (yield: 64.7%) of the desired product. Refractive index: 1.5933.

EXAMPLE 6 (Process C)

Preparation of ethyl 5-(4,6-dimethoxypyrimidin-2-yloxy)-3(4-methylphenyl)-2-methylthioimidazole-4-carboxylate (Compound No. 537)

30 ml of N,N-dimethylformamide was added to 2.0 g (49.7 mmol) of 5(4,6-dimethoxypyrimidin-2-yloxy)-3(4-methylphenyl)-2-methylthioimidazole-4-carboxylic acid and 0.8 g (5.79 mmol) of potassium carbonate, and the mixture was stirred at room temperature for 30 minutes. 0.9 g (5.77 mmol) of ethyl iodide was added thereto at room temperature, and the mixture was stirred further for 3 hours at room temperature and then poured into water. It was extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 1.86 g (yield: 86.9%) of the desired product. Melting point: 147°-148° C. EXAMPLE 7 (Process D)

Preparation of 4-heptylideneaminoester of 4-(4,6-dimethoxypyrimidin-2-yloxy)-2-phenylfuran-3-carboxylic acid (Compound No. 15)

1.7 g (5.0 mmol) of 4-(4,6-dimethoxypyrimidin-2-yloxy)-2-phenylfuran-3-carboxylic acid was dissolved in 20 ml of N,N-dimethylformamide, and 0.6 g (5.0 mmol) of 4-heptaneoxime and 0.8 g (10.0 mmol) of pyridine were added thereto. The mixture was cooled to 0° C., and 1.0 g (6.0 mmol) of dimethylamidephosphoryl dichloride was gradually dropwise added thereto with stirring. After the dropwise addition, it was stirred at room temperature for 3 hours. The reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.7 g (yield: 31.1%) of the desired product.

EXAMPLE 8 (Process E)

Preparation of 4-(4,6-dimethoxypyrimidin-2-yloxy)-3-methylisothiazole-5-carboxylic acid (Compound No. 480)

2.0 g (6.15 mmol) of ethyl 4-(4,6-dimethoxypyrimidin-2-yloxy)-3-methylisothiazole-5-carboxylate was dissolved in 20 ml of dimethylsulfoxide, and 3.1 ml (6.20 mmol) of a 2N sodium hydroxide aqueous solution was added thereto, followed by stirring at room temperature for 2 hours. The reaction solution was poured into water and adjusted to pH 3 to 4 with dilute hydrochloric acid, whereupon formed precipitates were collected by filtration, washed with water and then dried. Crude crystals were washed with hexane to obtain 1.7 g (yield: 94.4%) of the desired product. Melting point: 139°-141° C.

EXAMPLE 9 (Process F)

Preparation of sodium 3-(4,6-dimethoxypyrimidin-2-yloxy)-5-methylfuran-2-carboxylate (Compound No. 12)

30 ml of water was added to 2.07 ml (4.14 mmol) of a 2N sodium hydroxide aqueous solution, and 1.16 g (4.14 mmol) of 3-(4,6-dimethoxypyrimidin-2-yloxy)-5-methylfuran-2-carboxylic acid was added thereto at room temperature, followed by stirring for one hour. Then, the reaction solution was concentrated under reduced pressure to obtain 1.21 g (yield: 96.8%) of the desired product. Melting point: 225°-229.5° C.

EXAMPLE 10 (Process G)

Preparation of copper salt of 4-(4,6-dimethoxypyrimidin-2-yloxy)isoxazole-3-carboxylic acid (Compound No. 479)

20 ml of water was added to 0.80 ml (1.60 mmol) of a 2N sodium hydroxide aqueous solution, and 0.40 g (1.50 mmol) of 4(4,6-dimethoxypyrimidin-2-yloxy)isoxazole-3-carboxylic acid was added thereto at room temperature, followed by stirring for 30 minutes. Then, 0.30 g (1.88 mmol) of copper sulfate was dissolved in 10 ml of water and added thereto at room temperature, followed by stirring for 5 minutes. Precipitated crystals were collected by filtration to obtain 0.40 g (yield: 89.7%) of the desired product. Melting point: 148°-152° C.

EXAMPLE 11 (Process H)

Preparation of N-methylsulfonyl 4-(4,6-dimethoxypyrimidin-2-yloxy)-3-methylisothiazole-5-carbonamide (Compound No. 488)

10 ml of N,N-dimethylformamide was added to 0.68 g (2.29 mmol) of 4-(4,6-dimethoxypyrimidin-2-yloxy)-3-methylisothiazole-carboxylic acid and 0.41 g (2.53 mmol) of carbonyldiimidazole, and the mixture was stirred at room temperature for 3 hours. Then, 10 ml of N,N-dimethylformamide was added to 0.43 g (4.52 mmol) of methanesulfonamide and 0.18 g (4.50 mmol) of 60% sodium hydride, and the mixture was heated and stirred at from 80° to 90° C. for 2 hours and then added to the previously prepared dimethylformamide solution of carbonylimidazole at room temperature, and stirring was continued further at room temperature for 3 hours. The reaction solution was poured into water and washed with ethyl acetate. Then, the aqueous layer was acidified with a 10% HCl solution. Precipitated crystals were collected by filtration and washed with isopropyl ether to obtain 0.61 g (yield: 70.9%).

Now, compounds of the present invention are presented in Tables 1 to 60.

                                      TABLE 1                                      __________________________________________________________________________      ##STR13##                                                                                                     Physical nature                                Comp.                           mp (°C.)                                No. Xn   W Z   R.sup.1                                                                            R.sup.2                                                                             R       n.sub.D.sup.20                                 __________________________________________________________________________     1   H    O CH  OCH.sub.3                                                                          OCH.sub.3                                                                           OH                                                     2   5-CH.sub.3                                                                          O CH  OCH.sub.3                                                                          OCH.sub.3                                                                           OH      157-159                                        3   5-CH.sub.3                                                                          O CH  OCH.sub.3                                                                          OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       62-72                                          4   5-CH.sub.3                                                                          O CH  Cl  OCH.sub.3                                                                           OH                                                     5   5-CH.sub.3                                                                          O CH  Cl  OCH.sub.3                                                                           OCH.sub.3                                              6   H    S CH  OCH.sub.3                                                                          OCH.sub.3                                                                           OH                                                     7   H    S CH  OCH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                              8   H    S N   OCH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                              9   H    S N   OCH.sub.3                                                                          OCH.sub.3                                                                           OH                                                     10  H    O CH  OCH.sub.3                                                                          OCH.sub.3                                                                            ##STR14##                                             11  H    O CH  OCH.sub.3                                                                          OCH.sub.3                                                                           NHSO.sub.2 CH.sub.3                                    12  5-CH.sub.3                                                                          O CH  OCH.sub.3                                                                          OCH.sub.3                                                                           ONa       225-229.5                                    __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR15##                                                                                                         Physical nature                            Comp.                               mp (°C.)                            No. Xn      W Z  R.sup.1                                                                              R.sup.2                                                                            R        n.sub.D.sup.20                             __________________________________________________________________________     13                                                                                  ##STR16##                                                                             O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH       97-99                                      14                                                                                  ##STR17##                                                                             O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                           15                                                                                  ##STR18##                                                                             O CH OCH.sub.3                                                                            OCH.sub.3                                                                           ##STR19##                                                                              unmeasurable                               16                                                                                  ##STR20##                                                                             O CH Cl    OCH.sub.3                                                                          OH                                                  17                                                                                  ##STR21##                                                                             O CH                                                                                 ##STR22##                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                    18  2-CH.sub.3                                                                             O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                  19  2-CH.sub.3                                                                             O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                        86-90                                      20  2-CH.sub.3                                                                             S CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                  21  2-CH.sub.3                                                                             S CH Cl    OCH.sub.3                                                                          OCH.sub.3                                           __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR23##                                                                                                       Physical nature                              Comp.                             mp (°C.)                              No. Xn       W    Z  R.sup.1                                                                             R.sup.2                                                                            R   n.sub.D.sup.20                               __________________________________________________________________________     22  H        N    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH    199-200.5                                  23  H        NH   CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          151-152                                      24  H        NCH.sub.3                                                                           CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH  149-152                                      25  H        NCH.sub.3                                                                           CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          76-82                                        26                                                                                  ##STR24##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                               27                                                                                  ##STR25##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH  154-156                                      28                                                                                  ##STR26##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   1.5735                                       29                                                                                  ##STR27##                                                                              O    CH Cl   OCH.sub.3                                                                          OCH.sub.3                                        30                                                                                  ##STR28##                                                                              O    CH Cl   OCH.sub.3                                                                          OH                                               31                                                                                  ##STR29##                                                                              O    CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OCH.sub.3                                        32                                                                                  ##STR30##                                                                              O    CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OH                                               33                                                                                  ##STR31##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   88-90                                        34                                                                                  ##STR32##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                               35                                                                                  ##STR33##                                                                              S    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                               __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________                                     Physical nature                                Comp.                           mp (°C.)                                No.  Xn       W Z  R.sup.1                                                                             R.sup.2                                                                            R   n.sub.D.sup.20                                 __________________________________________________________________________     36                                                                                   ##STR34##                                                                              S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          37   4-CHCHCH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 38   4-CHCHCH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   1.5465                                         39   5-COOC.sub.2 H.sub.5                                                                    O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   1.5445                                         40   5-COOH   O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH  257-262                                        41   4-CH.sub.3,                                                                             O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   90-93                                               5-COOC.sub.2 H.sub.5                                                      42   4-CH.sub.3,                                                                             O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                               5-COOC.sub.2 H.sub.5                                                      43   H        S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 44   H        S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          45   H        S CH OCH.sub.3                                                                           OCH.sub. 3                                                                         OC.sub.2 H.sub.5                                   46   5-CH.sub.3                                                                              O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          47   5-CH.sub.3                                                                              O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 48   5-CH(CH.sub.3).sub.2                                                                    O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          49   5-CH(CH.sub.3).sub.2                                                                    O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 50                                                                                   ##STR35##                                                                              O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          51                                                                                   ##STR36##                                                                              O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 52   5-C(CH.sub.3).sub.3                                                                     O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          53   5-C(CH.sub.3).sub.3                                                                     O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 54                                                                                   ##STR37##                                                                              O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                          55                                                                                   ##STR38##                                                                              O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                 __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________                                       Physical nature                              Comp.                             mp (°C.)                              No. Xn  W          Z  R.sup.1                                                                            R.sup.2                                                                            R   n.sub.D.sup.20                               __________________________________________________________________________     56  5-Cl                                                                               O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.3 H.sub.7                                 57  5-Cl                                                                               O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               58  4-Cl                                                                               O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        59  4-Cl                                                                               O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               60  4,5-Cl.sub.2                                                                       O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        61  4,5-Cl.sub.2                                                                       O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               62  5-C.sub.2 F.sub.5                                                                  O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        63  5-C.sub.2 F.sub.5                                                                  O          CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               64  H   NCHO       CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        65  H   NCHO       CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               66  H   NCH.sub.2 CHCH.sub.2                                                                      CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        67  H   NCH.sub.2 CHCH.sub.2                                                                      CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               68  H   NCH.sub.2 CCH                                                                             CH OCH.sub. 3                                                                         OCH.sub.3                                                                          OC.sub.2 H.sub.5                                 69  H   NCH.sub.2 CCH                                                                             CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               70  H   NCH.sub.2 OCH.sub.3                                                                       CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        71  H   NCH.sub.2 OCH.sub.3                                                                       CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               72  H   NSO.sub.2 CH.sub.3                                                                        CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                 73  H   NSO.sub.2 CH.sub.3                                                                        CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               74  H   NCOCH.sub.3                                                                               CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        75  H   NCOCH.sub.3                                                                               CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               76  H                                                                                   ##STR39## CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        77  H                                                                                   ##STR40## CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               78  H                                                                                   ##STR41## CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                        79  H                                                                                   ##STR42## CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                               __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________                                         Physical nature                            Comp.                               mp (°C.)                            No. Xn                                                                               W  Z  R.sup.1                                                                            R.sup.2                                                                              R             n.sub.D.sup.20                             __________________________________________________________________________     80  H NH CH OCH.sub.3                                                                           ##STR43##                                                                           OK                                                       81  H NH CH OCH.sub.3                                                                           ##STR44##                                                                           O1/2Ca                                                   82  H NH CH OCH.sub.3                                                                           ##STR45##                                                                           ONH.sub.3 CH(CH.sub.3).sub.2                             83  H NH CH OCH.sub.3                                                                           ##STR46##                                                                           ONH.sub.4                                                84  H NH CH OCH.sub.3                                                                           ##STR47##                                                                           O1/3Fe                                                   85  H NH CH OCH.sub.3                                                                           ##STR48##                                                                           NHSO.sub.2 CH.sub.3                                      86  H NH CH OCH.sub.3                                                                          CF.sub.3                                                                             OCH.sub.3                                                87  H NH CH OCH.sub.3                                                                          CF.sub.3                                                                             OH                                                       88  H NH CH OCH.sub.3                                                                          CF.sub.3                                                                             OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                    89  H NH CH OCH.sub.3                                                                          SCH.sub.3                                                                            OC.sub.2 H.sub.5                                         90  H NH CH OCH.sub.3                                                                          SCH.sub. 3                                                                           OH                                                       91  H NH CH OCH.sub.3                                                                          SCH.sub.3                                                                            OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                    92  H NH CH OCH.sub.3                                                                          SCH.sub.3                                                                             ##STR49##                                               93  H NH CH OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                94  H NH CH OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                   OH                                                       95  H NH CH OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                   OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                    __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________                                            Physical nature                         Comp.                                  mp (°C.)                         No. Xn                                                                               W  Z  R.sup.1                                                                            R.sup.2  R             n.sub.D.sup.20                          __________________________________________________________________________      96 H NH CH CH.sub.3                                                                           CH.sub.3 OC.sub.4 H.sub.9                                       97 H NH CH CH.sub.3                                                                           CH.sub.3 OH                                                     98 H NH CH CH.sub.3                                                                           CH.sub.3                                                                                 ##STR50##                                             99 H NH CH CH.sub.3                                                                           CCCH.sub.3                                                                              OCH.sub.3                                             100 H NH CH CH.sub.3                                                                           CCCH.sub.3                                                                              OH                                                    101 H NH CH CH.sub.3                                                                           CCCH.sub.3                                                                              NHOCH.sub.2 CHCH.sub.2                                102 H NH CH CH.sub.3                                                                           CCCH.sub.3                                                                               ##STR51##                                            103 H NH CH OCH.sub.3                                                                          OCH.sub.2 CCH                                                                           OCH.sub.3                                             104 H NH CH OCH.sub.3                                                                          OCH.sub.2 CCH                                                                           OH                                                    105 H NH CH OCH.sub.3                                                                          OCH.sub.2 CCH                                                                            ##STR52##                                            106 H NH CH OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                             107 H NH CH OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                    OH                                                    108 H NH CH OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                    OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                 109 H NH CH OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                      OC.sub.2 H.sub.5                                      110 H NH CH OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                      OH                                                    111 H NH CH OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                       ##STR53##                                            112 H NH CH OCH.sub.3                                                                          NHCH.sub.3                                                                              OCH.sub.3                                             113 H NH CH OCH.sub.3                                                                          NHCH.sub.3                                                                              OH                                                    __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________                                     Physical nature                                Comp.                           mp (°C.)                                No.  Xn                                                                               W  Z R.sup.1                                                                            R.sup.2                                                                            R           n.sub.D.sup.20                                 __________________________________________________________________________     114  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3   190-192                                        115  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                         116  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                        117  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR54##                                                 118  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR55##                                                 119  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR56##                                                 120  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR57##                                                 121  H NH N OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                      122  H NH N CH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                           123  H NH N CH.sub.3                                                                           OCH.sub.3                                                                          OH                                                         124  H NH N CH.sub.3                                                                           OCH.sub.3                                                                          NHSO.sub.2 C.sub.2 H.sub.5                                 125  H NH N CH.sub.3                                                                           OCH.sub.3                                                                           ##STR58##                                                 126  H NH N CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                      127  H NH N CH.sub.3                                                                           OCH.sub.3                                                                           ##STR59##                                                 128  H NH N CH.sub.3                                                                           OCH.sub.3                                                                           ##STR60##                                                 129  H NH N CH.sub.3                                                                           OCH.sub.3                                                                           ##STR61##                                                 __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________                                      Physical nature                               Comp.                            mp (°C.)                               No. Xn                                                                               W  Z  R.sup.1                                                                             R.sup.2                                                                              R         n.sub.D.sup.20                                __________________________________________________________________________     130 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                            OCH.sub.3                                               131 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                            OH                                                      132 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                            OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                   133 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                            NHOCH.sub.3                                             134 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                             ##STR62##                                              135 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                             ##STR63##                                              136 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                            NHCH.sub.2 CCH                                          137 H NH N  OCHF.sub.2                                                                          OCH.sub.3                                                                            NHOCH.sub.2 CHCH.sub.2                                  138 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                           OC.sub.2 H.sub.5                                        139 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                           OH                                                      140 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                           OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                   141 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                           NHSO.sub.2 CH.sub.3                                     142 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                            ##STR64##                                              143 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                           NHOCH.sub.2 COOCH.sub.3                                 144 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                            ##STR65##                                              145 H NH CH OCHF.sub.2                                                                          OCHF.sub.2                                                                           ONa                                                     146 H NH CH OCH.sub.3                                                                            ##STR66##                                                                           OC.sub.3 H.sub.7                                        147 H NH CH OCH.sub.3                                                                            ##STR67##                                                                           OH                                                      148 H NH N  OCH.sub.3                                                                           CF.sub.3                                                                             OC.sub.2 H.sub.5                                        149 H NH N  OCH.sub.3                                                                           CF.sub.3                                                                             OH                                                      __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR68##                                                                                                       Physical nature                              Comp.                             mp (°C.)                              No. Xn       W    Z  R.sup.1                                                                             R.sup.2                                                                            R   n.sub.D.sup.20                               __________________________________________________________________________     150 4-CH.sub.3                                                                              NH   CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH  92-96                                        151 4-CH.sub.3                                                                              NH   CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   126-128                                      152 4-CH.sub.3                                                                              NCHO CH Cl   OCH.sub.3                                                                          OCH.sub.3                                        153 4-CH.sub.3                                                                              NCH.sub.3                                                                           CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH  156-159                                      154 4-CH.sub.3                                                                              NCH.sub.3                                                                           CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub. 2 H.sub.5                                                                  1.5487                                       155 4-CH.sub.3                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                               156 4-CH.sub.3                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                        157 H        O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   37-45                                        158 H        O    CH Cl   OCH.sub.3                                                                          OH                                               159 H        O    CH Cl   OCH.sub.3                                                                          OC.sub.2 H.sub.5                                 160 H        O    CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OH                                               161 H        O    CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OCH.sub.3                                        162                                                                                 ##STR69##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                               163                                                                                 ##STR70##                                                                              O    CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                 __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR71##                                                                                                        Physical nature                             Comp.                              mp (°C.)                             No. Xn            W Z  R.sup.1                                                                            R.sup.2                                                                            R   n.sup.20.sub.D                              __________________________________________________________________________     164                                                                                 ##STR72##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH  182-186                                     165                                                                                 ##STR73##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   161-165                                     166                                                                                 ##STR74##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              167                                                                                 ##STR75##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                       168 2-SO.sub.2 CH.sub.3                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH  172-184                                     169 2-CH.sub.2 SCH.sub.3                                                                         O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH  133-135                                     170 2-CH.sub.2 SCH.sub.3                                                                         O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   unmeasurable                                171                                                                                 ##STR76##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH  183-184                                     172                                                                                 ##STR77##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.5 H.sub.3                                                                   83-85                                       173                                                                                 ##STR78##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH  90-92                                       174                                                                                 ##STR79##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   unmeasurable                                175 2-CH.sub.3, 5-CH.sub.3                                                                       O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   1.5442                                      176                                                                                 ##STR80##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   1.5838                                      177                                                                                 ##STR81##    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                   43-47                                       __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________                                         Physical nature                            Comp.                               mp (°C.)                            No. Xn        W    Z  R.sup.1                                                                             R.sup.2                                                                             R   n.sup.20.sub.D                             __________________________________________________________________________     178                                                                                 ##STR82##                                                                               O    CH Cl   OCH.sub.3                                                                           OH                                             179                                                                                 ##STR83##                                                                               O    CH Cl   OCH.sub.3                                                                           OCH.sub.3                                      180                                                                                 ##STR84##                                                                               S    CH OCH.sub.3                                                                           OCH.sub.3                                                                           OH                                             181                                                                                 ##STR85##                                                                               S    CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                      182                                                                                 ##STR86##                                                                               NH   CH OCH.sub.3                                                                           OCH.sub.3                                                                           OH                                             183                                                                                 ##STR87##                                                                               NH   CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                      184                                                                                 ##STR88##                                                                               NCH.sub.3                                                                           CH OCH.sub.3                                                                           OCH.sub.3                                                                           OH                                             185                                                                                 ##STR89##                                                                               NCH.sub.3                                                                           CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                      186                                                                                 ##STR90##                                                                               O    N  OCH.sub.3                                                                           OCH.sub.3                                                                           OH                                             187                                                                                 ##STR91##                                                                               O    N  OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                      188                                                                                 ##STR92##                                                                               O    CH OCHF.sub.2                                                                          OCH.sub.3                                                                           OH                                             189                                                                                 ##STR93##                                                                               O    CH OCHF.sub.2                                                                          OCH.sub.3                                                                           OCH.sub.3                                      190                                                                                 ##STR94##                                                                               O    CH OCHF.sub.2                                                                          OCHF.sub.2                                                                          OH                                             191 2-CH(CH.sub.3).sub.2                                                                     S    CH OCH.sub.3                                                                           OCH.sub.3                                                                           OH                                             192 2-CH(CH.sub.3).sub.2                                                                     S    CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                      193 2-CH(CH.sub.3).sub.2                                                                     S    CH Cl   OCH.sub.3                                                                           OH                                             194 2-CH(CH.sub.3).sub.2                                                                     S    CH Cl   OCH.sub.3                                                                           OCH.sub.3                                      __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________                                        Physical nature                             Comp.                              mp (°C.)                             No. Xn         W    Z  R.sup.1                                                                            R.sup.2                                                                            R   n.sup.20.sub.D                              __________________________________________________________________________     195                                                                                 ##STR95## O    CH Cl  OCH.sub.3                                                                          OH                                              196                                                                                 ##STR96## S    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              197                                                                                 ##STR97## NH   CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              198                                                                                 ##STR98## NCH.sub.3                                                                           CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              199                                                                                 ##STR99## O    N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              200                                                                                 ##STR100##                                                                               O    N  CH.sub.3                                                                           OCH.sub.3                                                                          OH                                              201                                                                                 ##STR101##                                                                               O    CH CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       202                                                                                 ##STR102##                                                                               NH   CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                       203                                                                                 ##STR103##                                                                               NH   CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              204                                                                                 ##STR104##                                                                               NCH.sub.3                                                                           CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                       205                                                                                 ##STR105##                                                                               NCH.sub.3                                                                           CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                              206                                                                                 ##STR106##                                                                               O    CH CH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                207                                                                                 ##STR107##                                                                               O    CH CH.sub.3                                                                           OCH.sub.3                                                                          OH                                              208                                                                                 ##STR108##                                                                               O    CH CH.sub.3                                                                           CH.sub.3                                                                           OC.sub.3 H.sub.7                                209                                                                                 ##STR109##                                                                               O    CH CH.sub.3                                                                           CH.sub.3                                                                           OH                                              __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________                                          Physical nature                           Comp.                                mp (°C.)                           No. Xn     W Z  R.sup.1                                                                            R.sup.2                                                                            R            n.sup.20.sub.D                            __________________________________________________________________________     210                                                                                 ##STR110##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                   211                                                                                 ##STR111##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CCH                                          212                                                                                 ##STR112##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR113##                                            213                                                                                 ##STR114##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR115##                                            214                                                                                 ##STR116##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                       215                                                                                 ##STR117##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR118##                                            216                                                                                 ##STR119##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR120##                                            217                                                                                 ##STR121##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR122##                                            218                                                                                 ##STR123##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR124##                                            219                                                                                 ##STR125##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR126##                                            220                                                                                 ##STR127##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                    221                                                                                 ##STR128##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR129##                                            222                                                                                 ##STR130##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR131##                                            223                                                                                 ##STR132##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR133##                                            __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________                                          Physical nature                           Comp.                                mp (°C.)                           No. Xn     W Z  R.sup.1                                                                            R.sup.2                                                                            R            n.sup.20.sub.D                            __________________________________________________________________________     224                                                                                 ##STR134##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR135##                                            225                                                                                 ##STR136##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR137##                                            226                                                                                 ##STR138##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR139##                                            227                                                                                 ##STR140##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 SCH.sub.3                                    228                                                                                 ##STR141##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CN                                           229                                                                                 ##STR142##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 COOC.sub.2 H.sub.5                           230                                                                                 ##STR143##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 COOCH.sub.3                         231                                                                                 ##STR144##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR145##                                            232                                                                                 ##STR146##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR147##                                            233                                                                                 ##STR148##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHSO.sub.2 C.sub.2 H.sub.5                             234                                                                                 ##STR149##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR150##                                            235                                                                                 ##STR151##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR152##                                            236                                                                                 ##STR153##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                  237                                                                                 ##STR154##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NH.sub.2                                               __________________________________________________________________________

                                      TABLE 16                                     __________________________________________________________________________                                        Physical nature                             Comp.                              mp (°C.)                             No. Xn     W Z  R.sup.1                                                                            R.sup.2                                                                            R          n.sup.20.sub.D                              __________________________________________________________________________     238                                                                                 ##STR155##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOH                                                   239                                                                                 ##STR156##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOC.sub.2 H.sub.5                                     240                                                                                 ##STR157##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR158##                                            241                                                                                 ##STR159##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR160##                                            242                                                                                 ##STR161##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR162##                                            243                                                                                 ##STR163##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR164##                                            244                                                                                 ##STR165##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR166##                                            __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________                                            Physical nature                         Comp.                                  mp (°C.)                         No. Xn     W Z  R.sup.1                                                                            R.sup.2                                                                            R              n.sup.20.sub.D                          __________________________________________________________________________     245                                                                                 ##STR167##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR168##                                            246                                                                                 ##STR169##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR170##                                            247                                                                                 ##STR171##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR172##                                            248                                                                                 ##STR173##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR174##                                            249                                                                                 ##STR175##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR176##                                            250                                                                                 ##STR177##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR178##                                            251                                                                                 ##STR179##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR180##                                            252                                                                                 ##STR181##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR182##                                            253                                                                                 ##STR183##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR184##                                            254                                                                                 ##STR185##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHCH.sub.2 CH.sub.2 OCH.sub.3                          255                                                                                 ##STR186##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHCOCH.sub.3                                           __________________________________________________________________________

                                      TABLE 18                                     __________________________________________________________________________                                         Physical nature                            Comp.                               mp (°C.)                            No. Xn     W Z  R.sup.1                                                                            R.sup.2                                                                            R           n.sup.20.sub.D                             __________________________________________________________________________     256                                                                                 ##STR187##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHCH.sub.2 CHCH.sub.2                                  257                                                                                 ##STR188##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHCH.sub.2 C CH                                        258                                                                                 ##STR189##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOCH.sub.2 CHCH.sub.2                                 259                                                                                 ##STR190##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOCH.sub.2 C CH                                       260                                                                                 ##STR191##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR192##                                            261                                                                                 ##STR193##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR194##                                            262                                                                                 ##STR195##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR196##                                            263                                                                                 ##STR197##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOCH.sub.2 COOC.sub.2 H.sub.5                         264                                                                                 ##STR198##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR199##                                            265                                                                                 ##STR200##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR201##                                            266                                                                                 ##STR202##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR203##                                            267                                                                                 ##STR204##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR205##                                            __________________________________________________________________________

                                      TABLE 19                                     __________________________________________________________________________                                          Physical nature                           Comp.                                mp (°C.)                           No. Xn     W Z  R.sup.1                                                                            R.sup.2                                                                            R            n.sup.20.sub.D                            __________________________________________________________________________     268                                                                                 ##STR206##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHNH.sub.2                                             269                                                                                 ##STR207##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHNHCOCH.sub.3                                         270                                                                                 ##STR208##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR209##                                            271                                                                                 ##STR210##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR211##                                            272                                                                                 ##STR212##                                                                           O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR213##                                            273                                                                                 ##STR214##                                                                           O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR215##                                            274                                                                                 ##STR216##                                                                           O N  OCH.sub. 3                                                                         OCH.sub.3                                                                           ##STR217##                                            275                                                                                 ##STR218##                                                                           O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR219##                                            276                                                                                 ##STR220##                                                                           O N  OCH.sub.3                                                                          OCH.sub.3                                                                          NHSO.sub.2 C.sub.2 H.sub.5                             277                                                                                 ##STR221##                                                                           O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR222##                                            278                                                                                 ##STR223##                                                                           O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR224##                                            __________________________________________________________________________

                                      TABLE 20                                     __________________________________________________________________________                                         Physical nature                            Comp.                               mp (°C.)                            No. Xn     W Z  R.sup.1                                                                          R.sup.2                                                                            R             n.sup.20.sub.D                             __________________________________________________________________________     279                                                                                 ##STR225##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          OC.sub.2 H.sub.5                                         280                                                                                 ##STR226##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          OH                                                       281                                                                                 ##STR227##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                    282                                                                                 ##STR228##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR229##                                              283                                                                                 ##STR230##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                      284                                                                                 ##STR231##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR232##                                              285                                                                                 ##STR233##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                      286                                                                                 ##STR234##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHOCH.sub.2 CHCH.sub.2                                   287                                                                                 ##STR235##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR236##                                              288                                                                                 ##STR237##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR238##                                              289                                                                                 ##STR239##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR240##                                              290                                                                                 ##STR241##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR242##                                              291                                                                                 ##STR243##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR244##                                              __________________________________________________________________________

                                      TABLE 21                                     __________________________________________________________________________                                       Physical nature                              Comp.                             mp (°C.)                              No. Xn     W Z  R.sup.1                                                                          R.sup.2                                                                            R           n.sup.20.sub.D                               __________________________________________________________________________     292                                                                                 ##STR245##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR246##                                              293                                                                                 ##STR247##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          SC.sub.2 H.sub.5                                         294                                                                                 ##STR248##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR249##                                              295                                                                                 ##STR250##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR251##                                              296                                                                                 ##STR252##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR253##                                              297                                                                                 ##STR254##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR255##                                              298                                                                                 ##STR256##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR257##                                              299                                                                                 ##STR258##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR259##                                              300                                                                                 ##STR260##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR261##                                              301                                                                                 ##STR262##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR263##                                              302                                                                                 ##STR264##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR265##                                              303                                                                                 ##STR266##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          OCH.sub.2 COOCH.sub.3                                    304                                                                                 ##STR267##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHOCH.sub.2 COOC.sub.2 H.sub.5                           305                                                                                 ##STR268##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR269##                                              306                                                                                 ##STR270##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR271##                                              __________________________________________________________________________

                                      TABLE 22                                     __________________________________________________________________________                                     Physical nature                                Comp.                           mp (°C.)                                No. Xn     W Z  R.sup.1                                                                          R.sup.2                                                                            R         n.sup.20.sub.D                                 __________________________________________________________________________     307                                                                                 ##STR272##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR273##                                              308                                                                                 ##STR274##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHOH                                                     309                                                                                 ##STR275##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHCH.sub.2 C CH                                          310                                                                                 ##STR276##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHOCH.sub.2 C CH                                         311                                                                                 ##STR277##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHNH.sub.2                                               312                                                                                 ##STR278##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHNHCOCH.sub.3                                           313                                                                                 ##STR279##                                                                           O CH Cl                                                                               OCH.sub. 3                                                                          ##STR280##                                              314                                                                                 ##STR281##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR282##                                              315                                                                                 ##STR283##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHCOCH.sub.3                                             316                                                                                 ##STR284##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          NHCN                                                     317                                                                                 ##STR285##                                                                           O CH Cl                                                                               OCH.sub.3                                                                          H                                                        318                                                                                 ##STR286##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR287##                                              319                                                                                 ##STR288##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR289##                                              320                                                                                 ##STR290##                                                                           O CH Cl                                                                               OCH.sub.3                                                                           ##STR291##                                              __________________________________________________________________________

                                      TABLE 23                                     __________________________________________________________________________     Comp.                                    Physical nature                       No. X n     W Z  R.sup.1                                                                              R.sup.2                                                                            R             mp (°C.)                       __________________________________________________________________________                                              n.sub.D .sup.20                       321                                                                                 ##STR292##                                                                            O CH Cl    OCH.sub.3                                                                           ##STR293##                                         322                                                                                 ##STR294##                                                                            O CH Cl    OCH.sub.3                                                                           ##STR295##                                         323                                                                                 ##STR296##                                                                            O CH                                                                                 ##STR297##                                                                          OCH.sub.3                                                                          OCH.sub.3                                           324                                                                                 ##STR298##                                                                            O CH                                                                                 ##STR299##                                                                          OCH.sub.3                                                                          OH                                                  325                                                                                 ##STR300##                                                                            O CH                                                                                 ##STR301##                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3               326                                                                                 ##STR302##                                                                            O CH                                                                                 ##STR303##                                                                          OCH.sub.3                                                                           ##STR304##                                         327                                                                                 ##STR305##                                                                            O CH                                                                                 ##STR306##                                                                          OCH.sub.3                                                                           ##STR307##                                         328                                                                                 ##STR308##                                                                            O CH                                                                                 ##STR309##                                                                          OCH.sub.3                                                                           ##STR310##                                         329                                                                                 ##STR311##                                                                            O CH                                                                                 ##STR312##                                                                          OCH.sub.3                                                                          OCH.sub.2 C.sub.2 H.sub.5                           330                                                                                 ##STR313##                                                                            O CH                                                                                 ##STR314##                                                                          OCH.sub.3                                                                           ##STR315##                                         __________________________________________________________________________

                                      TABLE 24                                     __________________________________________________________________________     Comp.                                 Physical nature                          No. X n     W Z  R.sup.1                                                                              R.sup.2                                                                            R          mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     331                                                                                 ##STR316##                                                                            O CH                                                                                 ##STR317##                                                                          OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                 332                                                                                 ##STR318##                                                                            O CH                                                                                 ##STR319##                                                                          OCH.sub.3                                                                           ##STR320##                                         333                                                                                 ##STR321##                                                                            O CH                                                                                 ##STR322##                                                                          OCH.sub.3                                                                           ##STR323##                                         334                                                                                 ##STR324##                                                                            O CH                                                                                 ##STR325##                                                                          OCH.sub.3                                                                           ##STR326##                                         335                                                                                 ##STR327##                                                                            O CH                                                                                 ##STR328##                                                                          OCH.sub.3                                                                           ##STR329##                                         336                                                                                 ##STR330##                                                                            O CH                                                                                 ##STR331##                                                                          OCH.sub.3                                                                           ##STR332##                                         337                                                                                 ##STR333##                                                                            O CH                                                                                 ##STR334##                                                                          OCH.sub.3                                                                           ##STR335##                                         338                                                                                 ##STR336##                                                                            O CH                                                                                 ##STR337##                                                                          OCH.sub.3                                                                           ##STR338##                                         339                                                                                 ##STR339##                                                                            O CH                                                                                 ##STR340##                                                                          OCH.sub.3                                                                           ##STR341##                                         __________________________________________________________________________

                                      TABLE 25                                     __________________________________________________________________________     Comp.                                 Physical nature                          No. X n     W Z  R.sup.1                                                                              R.sup.2                                                                            R          mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     340                                                                                 ##STR342##                                                                            O CH                                                                                 ##STR343##                                                                          OCH.sub.3                                                                          SC.sub.3 H.sub.7                                    341                                                                                 ##STR344##                                                                            O CH                                                                                 ##STR345##                                                                          OCH.sub.3                                                                           ##STR346##                                         342                                                                                 ##STR347##                                                                            O CH                                                                                 ##STR348##                                                                          OCH.sub.3                                                                           ##STR349##                                         343                                                                                 ##STR350##                                                                            O CH                                                                                 ##STR351##                                                                          OCH.sub.3                                                                           ##STR352##                                         344                                                                                 ##STR353##                                                                            O CH                                                                                 ##STR354##                                                                          OCH.sub.3                                                                           ##STR355##                                         345                                                                                 ##STR356##                                                                            O CH                                                                                 ##STR357##                                                                          OCH.sub.3                                                                          OCH.sub.2 COOC.sub.2 H.sub.5                        346                                                                                 ##STR358##                                                                            O CH                                                                                 ##STR359##                                                                          OCH.sub.3                                                                          NHOCH.sub.2 CH.sub.3                                347                                                                                 ##STR360##                                                                            O CH                                                                                 ##STR361##                                                                          OCH.sub.3                                                                           ##STR362##                                         348                                                                                 ##STR363##                                                                            O CH                                                                                 ##STR364##                                                                          OCH.sub.3                                                                           ##STR365##                                         __________________________________________________________________________

                                      TABLE 26                                     __________________________________________________________________________     Comp.                                 Physical nature                          No. X n     W Z  R.sup.1                                                                              R.sup.2                                                                            R          mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     349                                                                                 ##STR366##                                                                            O CH                                                                                 ##STR367##                                                                          OCH.sub.3                                                                           ##STR368##                                         350                                                                                 ##STR369##                                                                            O CH                                                                                 ##STR370##                                                                          OCH.sub.3                                                                          NHOH                                                351                                                                                 ##STR371##                                                                            O CH                                                                                 ##STR372##                                                                          OCH.sub.3                                                                          NHOCH.sub.2 CHCH.sub.2                              352                                                                                 ##STR373##                                                                            O CH                                                                                 ##STR374##                                                                          OCH.sub.3                                                                          NHOCH.sub.2 C CH                                    353                                                                                 ##STR375##                                                                            O CH                                                                                 ##STR376##                                                                          OCH.sub.3                                                                          NHCH.sub.2 CHCH.sub.2                               354                                                                                 ##STR377##                                                                            O CH                                                                                 ##STR378##                                                                          OCH.sub.3                                                                          NHCH.sub.2 C CH                                     355                                                                                 ##STR379##                                                                            O CH                                                                                 ##STR380##                                                                          OCH.sub.3                                                                          NHNH.sub.2                                          356                                                                                 ##STR381##                                                                            O CH                                                                                 ##STR382##                                                                          OCH.sub.3                                                                           ##STR383##                                         __________________________________________________________________________

                                      TABLE 27                                     __________________________________________________________________________     Comp.                                     Physical nature                      No. X n     W Z  R.sup.1                                                                              R.sup.2                                                                            R              mp (°C.) n.sub.D              __________________________________________________________________________                                               .sup.20                              357                                                                                 ##STR384##                                                                            O CH                                                                                 ##STR385##                                                                          OCH.sub.3                                                                          NHCOCH.sub.3                                        358                                                                                 ##STR386##                                                                            O CH                                                                                 ##STR387##                                                                          OCH.sub.3                                                                          NHCN                                                359                                                                                 ##STR388##                                                                            O CH                                                                                 ##STR389##                                                                          OCH.sub.3                                                                          H                                                   360                                                                                 ##STR390##                                                                            O CH                                                                                 ##STR391##                                                                          OCH.sub.3                                                                           ##STR392##                                         361                                                                                 ##STR393##                                                                            O CH                                                                                 ##STR394##                                                                          OCH.sub.3                                                                           ##STR395##                                         362                                                                                 ##STR396##                                                                            O CH                                                                                 ##STR397##                                                                          OCH.sub.3                                                                           ##STR398##                                         363                                                                                 ##STR399##                                                                            O CH                                                                                 ##STR400##                                                                          OCH.sub.3                                                                           ##STR401##                                         364                                                                                 ##STR402##                                                                            O CH                                                                                 ##STR403##                                                                          OCH.sub.3                                                                           ##STR404##                                         365                                                                                 ##STR405##                                                                            O CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OCH.sub.3                                           366                                                                                 ##STR406##                                                                            O CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OH                                                  367                                                                                 ##STR407##                                                                            O CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 SI(CH.sub.3).sub.3               368                                                                                 ##STR408##                                                                            O CH OCHF.sub.2                                                                           OCH.sub.3                                                                           ##STR409##                                         369                                                                                 ##STR410##                                                                            O CH OCHF.sub.2                                                                           OCH.sub.3                                                                           ##STR411##                                         __________________________________________________________________________

                                      TABLE 28                                     __________________________________________________________________________     Comp.                                Physical nature                           No. X n     W Z  R.sup.1                                                                             R.sup.2                                                                            R          mp (°C.) n.sub.D .sup.20           __________________________________________________________________________     370                                                                                 ##STR412##                                                                            O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                  371                                                                                 ##STR413##                                                                            O CH OCHF.sub.2                                                                          OCH.sub.3                                                                           ##STR414##                                          372                                                                                 ##STR415##                                                                            O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          NHCN                                                 373                                                                                 ##STR416##                                                                            O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          NHOCH.sub.2 CHCH.sub.2                               374                                                                                 ##STR417##                                                                            O CH OCHF.sub.2                                                                          OCH.sub.3                                                                           ##STR418##                                          375                                                                                 ##STR419##                                                                            O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          NHOCH.sub.2 COOCH.sub.3                              376                                                                                 ##STR420##                                                                            S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                            377                                                                                 ##STR421##                                                                            S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                   378                                                                                 ##STR422##                                                                            S CH OCH.sub.3                                                                           OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                  379                                                                                 ##STR423##                                                                            S CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR424##                                          380                                                                                 ##STR425##                                                                            S CH OCH.sub.3                                                                           OCH.sub.3                                                                          ONa                                                  381                                                                                 ##STR426##                                                                            O N  OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                     382                                                                                 ##STR427##                                                                            O N  OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                   383                                                                                 ##STR428##                                                                            O N  OCH.sub.3                                                                           OCH.sub.3                                                                          ONa                                                  __________________________________________________________________________

                                      TABLE 29                                     __________________________________________________________________________     Comp.                                 Physical nature                          No. X n     W Z  R.sup.1                                                                            R.sup.2                                                                            R            mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     384                                                                                 ##STR429##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                    385                                                                                 ##STR430##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          ONH.sub.3 CH(CH.sub.3).sub.2                          386                                                                                 ##STR431##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          ONH.sub.4                                             387                                                                                 ##STR432##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR433##                                           388                                                                                 ##STR434##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          O1/2 Ca                                               389                                                                                 ##STR435##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR436##                                           390                                                                                 ##STR437##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                  391                                                                                 ##STR438##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR439##                                           392                                                                                 ##STR440##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                   393                                                                                 ##STR441##                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR442##                                           394                                                                                 ##STR443##                                                                            O N  CH.sub.3                                                                           OCH.sub.3                                                                           ##STR444##                                           395                                                                                 ##STR445##                                                                            O N  CH.sub.3                                                                           OCH.sub.3                                                                           ##STR446##                                           396                                                                                 ##STR447##                                                                            O N  CH.sub.3                                                                           OCH.sub.3                                                                           ##STR448##                                           397                                                                                 ##STR449##                                                                            O N  CH.sub.3                                                                           OCH.sub.3                                                                           ##STR450##                                           __________________________________________________________________________

                                      TABLE 30                                     __________________________________________________________________________     Comp.                                   Physical nature                        No. X n     W Z  R.sup.1                                                                             R.sup.2                                                                             R            mp (°C.)                        __________________________________________________________________________                                             n.sub.D .sup.20                        398                                                                                 ##STR451##                                                                            O N  CH.sub.3                                                                            OCH.sub.3                                                                            ##STR452##                                         399                                                                                 ##STR453##                                                                            O N  NHCH.sub.3                                                                          OCH.sub.3                                                                           OC.sub.3 H.sub.7                                    400                                                                                 ##STR454##                                                                            O N  NHCH.sub.3                                                                          OCH.sub.3                                                                           OH                                                  401                                                                                 ##STR455##                                                                            O N  NHCH.sub.3                                                                          NHCH.sub.3                                                                          OC.sub.4 H.sub.9                                    402                                                                                 ##STR456##                                                                            O N  NHCH.sub.3                                                                          NHCH.sub.3                                                                          OH                                                  403                                                                                 ##STR457##                                                                            O N  NHCH.sub.3                                                                          NHCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                 404                                                                                 ##STR458##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                            ##STR459##                                         405                                                                                 ##STR460##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                            ##STR461##                                         406                                                                                 ##STR462##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3               407                                                                                 ##STR463##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                408                                                                                 ##STR464##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.2 C CH                                      409                                                                                 ##STR465##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                           SC.sub.2 H.sub.5                                    410                                                                                 ##STR466##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                            ##STR467##                                         411                                                                                 ##STR468##                                                                            O CH OCH.sub.3                                                                           OCH.sub.3                                                                            ##STR469##                                         __________________________________________________________________________

                                      TABLE 31                                     __________________________________________________________________________     Comp.                                 Physical nature                          No. X n     W Z  R.sup.1                                                                            R.sup.2                                                                            R            mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     412                                                                                 ##STR470##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR471##                                           413                                                                                 ##STR472##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR473##                                           414                                                                                 ##STR474##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                   415                                                                                 ##STR475##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CN                                          416                                                                                 ##STR476##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 COOCH.sub.3                                 417                                                                                 ##STR477##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR478##                                           418                                                                                 ##STR479##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHSO.sub.2 C.sub.2 H.sub.5                            419                                                                                 ##STR480##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR481##                                           420                                                                                 ##STR482##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR483##                                           421                                                                                 ##STR484##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NH.sub.2                                              422                                                                                 ##STR485##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOH                                                  423                                                                                 ##STR486##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOCH.sub.3                                           424                                                                                 ##STR487##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR488##                                           425                                                                                 ##STR489##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOCH.sub.2 CHCH.sub.2                                __________________________________________________________________________

                                      TABLE 32                                     __________________________________________________________________________     Comp.                                 Physical nature                          No. X n     W Z  R.sup.1                                                                            R.sup.2                                                                            R            mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     426                                                                                 ##STR490##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR491##                                           427                                                                                 ##STR492##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR493##                                           428                                                                                 ##STR494##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          NHOCH.sub.2 COOCH.sub.3                               429                                                                                 ##STR495##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR496##                                           430                                                                                 ##STR497##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR498##                                           431                                                                                 ##STR499##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 Si(CH.sub.3).sub.3                 432                                                                                 ##STR500##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                  433                                                                                 ##STR501##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR502##                                           434                                                                                 ##STR503##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR504##                                           435                                                                                 ##STR505##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 OCH.sub.3                                   436                                                                                 ##STR506##                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                  __________________________________________________________________________

                                      TABLE 33                                     __________________________________________________________________________      ##STR507##                                                                    Comp.                                     Physical nature                      No. X n    W     Z  R.sup.1                                                                            R.sup.2                                                                            R.sup.3   R   mp (°C.) n.sub.D              __________________________________________________________________________                                               .sup.20                              437 5-CH.sub.3                                                                            O     CH OCH.sub.3                                                                          OCH.sub.3                                                                          H         OH  157-159                              438 5-CH.sub.3                                                                            O     CH OCH.sub.3                                                                          OCH.sub.3                                                                          N         OC.sub.2 H.sub.5                                                                   159-161                              439 4-COOC.sub.2 H.sub.5                                                                  O     CH OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3  OC.sub.2 H.sub.5                                                                   103-104                              440 4-COOC.sub.2 H.sub.5                                                                  O     CH OCH.sub.3                                                                          OCH.sub.3                                                                          H         OC.sub.2 H.sub.5                                                                   159-161                              441 H      O     N  OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3  OCH.sub.3                                442 H      O     N  OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3  OH                                       443 H      S     CH OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3  OCH.sub.3                                444 H      S     CH OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3  OH                                       445 H      S     CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR508##                                                                              OH                                       446 H      S     CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR509##                                                                              OCH.sub.3                                447 H      O     CH Cl  OCH.sub.3                                                                           ##STR510##                                                                              OH                                       448 H      O     CH Cl  OCH.sub.3                                                                           ##STR511##                                                                              OC.sub.2 H.sub.5                         449 H      NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR512##                                                                              OH                                       450 H      NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR513##                                                                              OCH.sub.3                                451 H      NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR514##                                                                              OCH.sub.3                                __________________________________________________________________________

                  TABLE 34                                                         ______________________________________                                          ##STR515##                                                                                                               Physical                                                                       nature                              Comp.                                      mp (°C.)                     No.    X      W     Z    R.sup.1                                                                              R.sup.2                                                                              R     n.sub.D .sup.20                     ______________________________________                                         452    CH.sub.3                                                                              O     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OH    155-158                             453    CH.sub.3                                                                              O     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     1.5133                              454    CH.sub.3                                                                              O     N    OCH.sub.3                                                                            OCH.sub.3                                                                            OH                                        455    CH.sub.3                                                                              O     N    OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                 456    CH.sub.3                                                                              O     CH   Cl    OCH.sub.3                                                                            OH                                        457    CH.sub.3                                                                              O     CH   Cl    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          ______________________________________                                    

                                      TABLE 35                                     __________________________________________________________________________      ##STR516##                                                                    Comp.                                 Physical nature                          No. X n    W     Z  R.sup.1                                                                            R.sup.2                                                                            R         mp (°C.) n.sub.D .sup.20          __________________________________________________________________________     458 CH.sub.3                                                                              NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3 175-176                                  459 CH.sub.3                                                                              NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH        219-222                                  460 CH.sub.3                                                                              NCH.sub.3                                                                            CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH        147-149                                  461                                                                                 ##STR517##                                                                           NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3   152-154.5                              462                                                                                 ##STR518##                                                                           NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH        200-204                                  463                                                                                 ##STR519##                                                                           NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR520##                                        464                                                                                 ##STR521##                                                                           NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 465                                                                                 ##STR522##                                                                           S     CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 466                                                                                 ##STR523##                                                                           S     CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          467                                                                                 ##STR524##                                                                           S     CH Cl  OCH.sub.3                                                                          OH                                                 468                                                                                 ##STR525##                                                                           S     CH Cl  OCH.sub.3                                                                          OCH.sub.3                                          469                                                                                 ##STR526##                                                                           S     CH CH.sub.3                                                                           CH.sub.3                                                                           OH                                                 470                                                                                 ##STR527##                                                                           S     CH CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                          __________________________________________________________________________

                  TABLE 36                                                         ______________________________________                                          ##STR528##                                                                                                                Physical                                                                       nature                             Comp.                                       mp (°C.)                    No.   X     W        Z    R.sup.1                                                                              R.sup.2                                                                              R     n.sub.D .sup.20                    ______________________________________                                         471   H     O        CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OH    159-160                            472   H     O        CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     81-83                              473   H     S        CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OH                                       474   H     S        CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                475   H     NH       CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OH                                       476   H     NCHO     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                477   H     O        CH   Cl    OCH.sub.3                                                                            OH                                       478   H     O        CH   Cl    OCH.sub.3                                                                            OC.sub.2 H.sub.5                         479   H     O        CH   OCH.sub.3                                                                            OCH.sub.3                                                                            O1/2Cu                                                                               148-152                            ______________________________________                                    

                                      TABLE 37                                     __________________________________________________________________________      ##STR529##                                                                    Comp.                             Physical nature                              No. X  W Z  R.sup.1                                                                             R.sup.2                                                                            R            mp (°C.) n.sub.D .sup.20              __________________________________________________________________________     480 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH           139-141                                      481 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                            63-66                                        482 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.4 H.sub.9                                          483 CH.sub.3                                                                          O CH Cl   OCH.sub.3                                                                          OC.sub.3 H.sub.7                                          484 CH.sub.3                                                                          O CH Cl   OCH.sub.3                                                                          OH                                                        485 CH.sub.3                                                                          O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OCH.sub.3                                                 486 CH.sub.3                                                                          O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OH                                                        487 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR530##                                               488 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                                                         145-148                                      489 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                          NHSO.sub.2 C.sub.3 H.sub.7                                490 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR531##                                               491 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR532##                                               492 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR533##                                               493 CH.sub.3                                                                          O CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR534##                                               __________________________________________________________________________

                                      TABLE 38                                     __________________________________________________________________________                                      Physical nature                               Comp.                            mp (°C.)                               No. X  W Z  R.sup.1                                                                            R.sup.2                                                                            R            n.sub.D.sup.20                                __________________________________________________________________________     494 CH.sub.3                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR535##                                                495 CH.sub.3                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR536##                                                496 CH.sub.3                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR537##                                                497 CH.sub.3                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR538##                                                __________________________________________________________________________

                                      TABLE 39                                     __________________________________________________________________________      ##STR539##                                                                                                       Physical nature                             Comp.                              mp (°C.)                             No. X  W    Z  R.sup.1                                                                              R.sup.2                                                                            R         n.sub.D.sup.20                              __________________________________________________________________________     498 CH.sub.3                                                                          NCH.sub.3                                                                           CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH        146-149                                     499 CH.sub.3                                                                          NCH.sub.3                                                                           CH OCH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                          96-100                                     500 CH.sub.3                                                                          NCH.sub.3                                                                           CH Cl    OCH.sub.3                                                                          OCH.sub.3                                             501 CH.sub.3                                                                          NCH.sub.3                                                                           CH Cl    OCH.sub.3                                                                          OH                                                    502 CH.sub.3                                                                          NCH.sub.3                                                                           CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OCH.sub.3                                             503 CH.sub.3                                                                          NCH.sub.3                                                                           CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OH                                                    504 CH.sub.3                                                                          NCH.sub.3                                                                           CH                                                                                 ##STR540##                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                      505 CH.sub.3                                                                          NCH.sub.3                                                                           CH                                                                                 ##STR541##                                                                          OCH.sub.3                                                                          OH                                                    506 CH.sub.3                                                                          NCH.sub.3                                                                           N  OCH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.3 H.sub.7                                      507 CH.sub.3                                                                          NCH.sub.3                                                                           N  OCH.sub.3                                                                            OCH.sub.3                                                                           ##STR542##                                           508 CH.sub.3                                                                          NCH.sub.3                                                                           N  OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                    __________________________________________________________________________

                                      TABLE 40                                     __________________________________________________________________________      ##STR543##                                                                                                        Physical nature                            Comp.                               mp (°C.)                            No. X      W Z  R.sup.1                                                                              R.sup.2                                                                            R         n.sub.D.sup.20                             __________________________________________________________________________     509 CH.sub.3                                                                              O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                     510 CH.sub.3                                                                              O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                   511 CH.sub.3                                                                              O CH OCH.sub.3                                                                            OCH.sub.3                                                                           ##STR544##                                          512 CH.sub.3                                                                              O CH Cl    OCH.sub.3                                                                          OCH.sub.3                                            513 CH.sub.3                                                                              O CH Cl    OCH.sub.3                                                                          OH                                                   514 CH.sub.3                                                                              O CH                                                                                 ##STR545##                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                     515 CH.sub. 3                                                                             O CH                                                                                 ##STR546##                                                                          OCH.sub.3                                                                          OH                                                   516                                                                                 ##STR547##                                                                           O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                            517                                                                                 ##STR548##                                                                           O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                   __________________________________________________________________________

                  TABLE 41                                                         ______________________________________                                          ##STR549##                                                                                                              Physical                                                                       nature                               Comp.                                     mp (°C.)                      No.   X     W     Z    R.sup.1                                                                              R.sup.2                                                                              R      n.sub.D.sup.20                       ______________________________________                                         518   H     S     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                                                                             233-239                              519   H     S     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            OC.sub.2 H.sub.5                            520   H     S     CH   Cl    OCH.sub.3                                                                            OCH.sub.3                                   521   H     S     CH   CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                   522   H     S     N    OCH.sub.3                                                                            OCH.sub.3                                                                            OC.sub.2 H.sub.5                            ______________________________________                                    

                                      TABLE 42                                     __________________________________________________________________________      ##STR550##                                                                                                        Physical nature                            Comp.                               mp (°C.)                            No. X    W Z  R.sup.1                                                                            R.sup.2                                                                            R             n.sub.D.sup.20                             __________________________________________________________________________     523 CH.sub.3                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                             93-94                                      524 CH.sub.3                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                       525 CH.sub.3                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR551##                                              526 CH.sub.3                                                                            O N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR552##                                              527 CH.sub.3                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.3 H.sub.7                                         528 CH.sub.3                                                                            O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                       529 CH.sub.2 S                                                                          S N  OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                             121-123                                    530 CH.sub.2 S                                                                          S N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                       531 CH.sub.2 S                                                                          S N  OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR553##                                              532 CH.sub.2 S                                                                          S N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                533 CH.sub.2 S                                                                          S CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                             95-98                                      534 CH.sub.2 S                                                                          S CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR554##                                              535 CH.sub.2 S                                                                          S CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR555##                                              __________________________________________________________________________

                                      TABLE 43                                     __________________________________________________________________________      ##STR556##                                                                                                            Physical nature                        Comp.                                   mp (°C.)                        No. X    W Z  R.sup.1                                                                            R.sup.2                                                                            R.sup.3   R       n.sub.D.sup.20                         __________________________________________________________________________     536 CH.sub.3 S                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR557##                                                                              OH      154-157                                537 CH.sub.3 S                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR558##                                                                              OC.sub.2 H.sub.5                                                                       147-148                                538 CH.sub.3 S                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR559##                                                                               ##STR560##                                    539 CH.sub.3 S                                                                          O CH Cl  OCH.sub.3                                                                           ##STR561##                                                                              OCH.sub.3                                      540 CH.sub.3 S                                                                          O CH Cl  OCH.sub.3                                                                           ##STR562##                                                                              OH                                             541 CH.sub.3 S                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR563##                                                                              ONa                                            542 CH.sub.3 S                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR564##                                                                              O1/2Ca                                         543 CH.sub.3 S                                                                          O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR565##                                                                               ##STR566##                                    __________________________________________________________________________

                                      TABLE 44                                     __________________________________________________________________________      ##STR567##                                                                                                       Physical nature                             Comp.                              mp (°C.)                             No. W Z  R.sup.1                                                                            R.sup.2                                                                            R.sup.3      R    n.sub.D.sup.20                              __________________________________________________________________________     544 O CH OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3     OH                                               545 O CH OCH.sub.3                                                                          OCH.sub.3                                                                          CH.sub.3     OCH.sub.3                                        546 O CH OCH.sub.3                                                                          OCH.sub.3                                                                          H            OH                                               547 O CH OCH.sub.3                                                                          OCH.sub.3                                                                          H            OC.sub.2 H.sub.5                                 548 O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR568##  H                                                549 O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR569##  OH                                               550 S CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR570##  H                                                551 S CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR571##  OH                                               552 O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR572##  H                                                553 O CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR573##  OH                                               554 S CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR574##  H                                                555 S CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR575##  OH                                               __________________________________________________________________________

                                      TABLE 45                                     __________________________________________________________________________      ##STR576##                                                                                                   Physical nature                                 Comp.                          mp (°C.)                                 No. Xn      W  Z  R.sup.1                                                                            R.sup.2                                                                            R    n.sub.D.sup.20                                  __________________________________________________________________________     556 H       O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    1.5389                                          557 H       O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                   558 H       S  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                            559 H       S  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                   560 H       NH CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                     561 H       NH CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                   562                                                                                 ##STR577##                                                                            O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    105-108                                         563                                                                                 ##STR578##                                                                            O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                   564                                                                                 ##STR579##                                                                            S  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                    135-137                                         565                                                                                 ##STR580##                                                                            S  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH   185-187                                         566                                                                                 ##STR581##                                                                            S  N  OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                     567                                                                                 ##STR582##                                                                            O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                            568                                                                                 ##STR583##                                                                            O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                   569 H       O  CH Cl  OCH.sub.3                                                                          OH                                                   __________________________________________________________________________

                                      TABLE 46                                     __________________________________________________________________________                                       Physical nature                              Comp.                             mp (°C.)                              No. Xn         W Z  R.sup.1                                                                             R.sup.2                                                                            R    n.sub.D.sup.20                               __________________________________________________________________________     570 H          O CH Cl   OCH.sub.3                                                                          OC.sub.2 H.sub.5                                  571 H          O CH CH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                  572 H          O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                  573 H          O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OH                                                574 2-CH.sub.3 O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                  575 2-CH.sub.3 O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                576 2-CH.sub.3 O CH Cl   OCH.sub.3                                                                          OCH.sub.3                                         577 2-CH.sub.3 O CH Cl   OCH.sub.3                                                                          OH                                                578                                                                                 ##STR584##                                                                               S CH OCH3 OCH.sub.3                                                                          OCH.sub.3                                         579                                                                                 ##STR585##                                                                               S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                580                                                                                 ##STR586##                                                                               O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                  581                                                                                 ##STR587##                                                                               O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                582 6-Cl       O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                         583 6-Cl       O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                584 6-Cl       O N  OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                         585 6-Cl       O N  OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                586 6-Cl       S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                         587 6-Cl       S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                588 6-Cl       S N  OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                         589 6-Cl       S N  OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                __________________________________________________________________________

                                      TABLE 47                                     __________________________________________________________________________                                     Physical nature                                Comp.                           mp (°C.)                                No. Xn         W Z  R.sup.1                                                                            R.sup.2                                                                            R   n.sub.D.sup.20                                 __________________________________________________________________________     590 6-OC.sub.2 H.sub.5                                                                        O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          591 6-OC.sub.2 H.sub.5                                                                        O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 592 6-OC.sub.2 H.sub.5                                                                        O N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          593 6-OC.sub.2 H.sub.5                                                                        O N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 594 6-OC.sub.2 H.sub.5                                                                        S CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          595 6-OC.sub.2 H.sub.5                                                                        S CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 596                                                                                 ##STR588##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          597                                                                                 ##STR589##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 598                                                                                 ##STR590##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          599                                                                                 ##STR591##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 600                                                                                 ##STR592##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          601                                                                                 ##STR593##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 602 6-NHCH(CH.sub.3).sub.2                                                                    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          603 6-NHCH(CH.sub.3).sub.2                                                                    O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 604                                                                                 ##STR594##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          605                                                                                 ##STR595##                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 606 6-SCH.sub.3                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          607 6-SCH.sub.3                                                                               O CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 __________________________________________________________________________

                                      TABLE 48                                     __________________________________________________________________________                                     Physical nature                                Comp.                           mp (°C.)                                No. Xn        W  Z  R.sup.1                                                                            R.sup.2                                                                            R   n.sub.D.sup.20                                 __________________________________________________________________________     608                                                                                 ##STR596##                                                                              O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          609                                                                                 ##STR597##                                                                              O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 610 6-SO.sub.2 CH.sub.3                                                                      O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          611 6-SO.sub.2 CH.sub.3                                                                      O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 612                                                                                 ##STR598##                                                                              O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          613                                                                                 ##STR599##                                                                              O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 614                                                                                 ##STR600##                                                                              O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          615                                                                                 ##STR601##                                                                              O  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 616                                                                                 ##STR602##                                                                              NH CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          617                                                                                 ##STR603##                                                                              NH CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 618                                                                                 ##STR604##                                                                              O  N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                          619                                                                                 ##STR605##                                                                              O  N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                 620                                                                                 ##STR606##                                                                              O  CH Cl  OCH.sub.3                                                                          OCH.sub.3                                          621                                                                                 ##STR607##                                                                              O  CH Cl  OCH.sub.3                                                                          OH                                                 __________________________________________________________________________

                                      TABLE 49                                     __________________________________________________________________________      ##STR608##                                                                                                  Physical nature                                  Comp.                         mp (°C.)                                  No. Xn                                                                               W Z  R.sup.1                                                                             R.sup.2                                                                            R         n.sub.D.sup.20                                   __________________________________________________________________________     622 H O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3 88-93                                            623 H O CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                         624 H S CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR609##                                                                              115-117                                          625 H S CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH        136-138                                          626 H S N  OCH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                           627 H S N  OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                         628 H O CH Cl   OCH.sub.3                                                                          OCH.sub.3                                                  629 H O CH Cl   OCH.sub.3                                                                          OH                                                         630 H O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OC.sub.3 H.sub.7                                           631 H O CH OCHF.sub.2                                                                          OCH.sub.3                                                                          OH                                                         632 H O N  CH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                           633 H O N  CH.sub.3                                                                            OCH.sub.3                                                                          OH                                                         __________________________________________________________________________

                                      TABLE 50                                     __________________________________________________________________________      ##STR610##                                                                                                     Physical nature                               Comp.                            mp (°C.)                               No. Xn                                                                               W     Z  R.sup.1                                                                            R.sup.2                                                                            R         n.sub.D.sup.20                                __________________________________________________________________________     634 H NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                        635 H NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                      636 H NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                               637 H NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR611##                                             638 H NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                      639 H NH    N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                      640 H NH    N  OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                                        641 H NCH.sub.3                                                                            N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub. 3                                              642 H NCH.sub.3                                                                            N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                                      643 H NCHO  N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                               644 H NCH.sub.3                                                                            N  CH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                                        645 H NCH.sub.3                                                                            N  CH.sub.3                                                                           OCH.sub.3                                                                          OH                                                      __________________________________________________________________________

                                      TABLE 51                                     __________________________________________________________________________      ##STR612##                                                                                                                  Physical nature                  Comp.                                         mp (°C.)                  No. Xn             W     Z  R.sup.1                                                                            R.sup.2                                                                            R         n.sub.D.sup.20                   __________________________________________________________________________     646 H              NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                           647 H              NH    CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                         648 H              NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                  649 H              NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                           ##STR613##                                650 H              NCHO  CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                         651 H              NH    N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                         652 H              NH    N  OCH.sub.3                                                                          OCH.sub.3                                                                          OC.sub.2 H.sub.5                           653 H              NCH.sub.3                                                                            N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                  654 H              NCH.sub.3                                                                            N  OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                         655 H              NCHO  N  OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                  656 H              NCH.sub.3                                                                            N  CH.sub.3                                                                           OCH.sub.3                                                                          OC.sub.2 H.sub.5                           657 H              NCH.sub.3                                                                            N  CH.sub.3                                                                           OCH.sub.3                                                                          OH                                         658                                                                                 ##STR614##    O     CH OCH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                  659                                                                                 ##STR615##    O     CH OCH.sub.3                                                                          OCH.sub.3                                                                          OH                                         __________________________________________________________________________

                                      TABLE 52                                     __________________________________________________________________________      ##STR616##                                                                                                     Physical nature                               Comp.                            mp (°C.)                               No. X   W Z  R.sup.1                                                                              R.sup.2                                                                            R         n.sub.D.sup.20                                __________________________________________________________________________     660 CH.sub.3 S                                                                         O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                         1.5628                                        661 CH.sub.3 S                                                                         O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                      662 CH.sub.3 S                                                                         O CH Cl    OCH.sub.3                                                                          OCH.sub.3                                               663 CH.sub.3 S                                                                         O CH Cl    OCH.sub.3                                                                          OH                                                      664 CH.sub.3 S                                                                         O CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OCH.sub.3                                               665 CH.sub.3 S                                                                         O CH OCHF.sub.2                                                                           OCH.sub.3                                                                          OH                                                      666 CH.sub.3                                                                           O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.3 H.sub.7                                        667 CH.sub.3                                                                           O CH OCH.sub.3                                                                            OCH.sub.3                                                                           ##STR617##                                             668 CH.sub.3                                                                           O CH OCH.sub.3                                                                            OCH.sub.3                                                                          OH                                                      669 CH.sub.3                                                                           O CH Cl    OCH.sub.3                                                                          OC.sub.4 H.sub.5                                        670 CH.sub.3                                                                           O CH Cl    OCH.sub.3                                                                          OCH(CH.sub.3).sub.2                                     671 CH.sub.3                                                                           O CH Cl    OCH.sub.3                                                                          OH                                                      672 CH.sub.3                                                                           O CH                                                                                 ##STR618##                                                                          OCH.sub.3                                                                          OC.sub.3 H.sub.7                                        673 CH.sub.3                                                                           O CH                                                                                 ##STR619##                                                                          OCH.sub.3                                                                          OH                                                      __________________________________________________________________________

                                      TABLE 53                                     __________________________________________________________________________      ##STR620##                                                                                                     Physical nature                               Comp.                            mp (°C.)                               No.  Xn                                                                               W  Z  R.sup.1                                                                             R.sup.2                                                                            R          n.sub.D.sup.20                                __________________________________________________________________________     674  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3  135-138                                       675  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH         154-159                                       676  H O  CH Cl   OCH.sub.3                                                                          OC.sub.2 H.sub.5                                         677  H O  CH Cl   OCH.sub.3                                                                          OH                                                       678  H O  CH CH.sub.3                                                                            CH.sub.3                                                                           OC.sub.3 H.sub.7                                         679  H O  CH CH.sub.3                                                                            CH.sub.3                                                                           OH                                                       680  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR621##                                              681  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                      682  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR622##                                              683  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR623##                                              684  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR624##                                              685  H O  N  OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                686  H O  N  OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                       687  H O  N  CH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                         688  H O  N  CH.sub.3                                                                            OCH.sub.3                                                                          OH                                                       689  H S  CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                __________________________________________________________________________

                  TABLE 54                                                         ______________________________________                                                                                     Physical                                                                       nature                             Comp.                                       mp (°C.)                    No.   Xn    W     Z    R.sup.1 R.sup.2                                                                               R     n.sub.D.sup.20                     ______________________________________                                         690   H     S     CH   OCH.sub.3                                                                              OCH.sub.3                                                                             OH                                       691   H     S     CH   Cl      OCH.sub.3                                                                             OCH.sub.3                                692   H     S     CH   Cl      OCH.sub.3                                                                             OH                                       693   H     S     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OCH.sub.3                                694   H     O     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OH                                       695   H     O     CH   OCHF.sub.2                                                                             OCHF.sub.2                                                                            OCH.sub.3                                696   H     O     CH   OCHF.sub.2                                                                             OCHF.sub.2                                                                            OH                                       697   H     O     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OCH.sub.3                                698   H     O     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OH                                       699   H     O     CH                                                                                   ##STR625##                                                                            OCH.sub.3                                                                             OC.sub.2 H.sub.5                         700   H     O     CH                                                                                   ##STR626##                                                                            OCH.sub.3                                                                             OH                                       701   H     O     CH   SCH.sub.3                                                                              OCH.sub.3                                                                             OC.sub.3 H.sub.7                         702   H     O     CH   SCH.sub.3                                                                              OCH.sub.3                                                                             OH                                       ______________________________________                                    

                                      TABLE 55                                     __________________________________________________________________________      ##STR627##                                                                                                     Physical nature                               Comp.                            mp (°C.)                               No.  Xn                                                                               W  Z  R.sup.1                                                                             R.sup.2                                                                            R          n.sub.D.sup.20                                __________________________________________________________________________     703  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3  133-136                                       704  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                          OH         143-146                                       705  H O  CH Cl   OCH.sub.3                                                                          OC.sub.2 H.sub.5                                         706  H O  CH Cl   OCH.sub.3                                                                          OH                                                       707  H O  CH CH.sub.3                                                                            CH.sub.3                                                                           OC.sub.3 H.sub.7                                         708  H O  CH CH.sub.3                                                                            CH.sub.3                                                                           OH                                                       709  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR628##                                              710  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                      711  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR629##                                              712  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR630##                                              713  H O  CH OCH.sub.3                                                                           OCH.sub.3                                                                           ##STR631##                                              714  H O  N  OCH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                                715  H O  N  OCH.sub.3                                                                           OCH.sub.3                                                                          OH                                                       716  H O  N  CH.sub.3                                                                            OCH.sub.3                                                                          OC.sub.2 H.sub.5                                         717  H O  N  CH.sub.3                                                                            OCH.sub.3                                                                          OH                                                       __________________________________________________________________________

                  TABLE 56                                                         ______________________________________                                                                                     Physical                                                                       nature                             Comp.                                       mp (°C.)                    No.   Xn    W     Z    R.sup.1 R.sup.2                                                                               R     n.sub.D.sup.20                     ______________________________________                                         718   H     S     CH   OCH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                719   H     S     CH   OCH.sub.3                                                                              OCH.sub.3                                                                             OH                                       720   H     S     CH   Cl      OCH.sub.3                                                                             OCH.sub.3                                721   H     S     CH   Cl      OCH.sub.3                                                                             OH                                       722   H     S     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OCH.sub.3                                723   H     S     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OH                                       724   H     O     CH   OCHF.sub.2                                                                             OCHF.sub.2                                                                            OCH.sub.3                                725   H     O     CH   OCHF.sub.2                                                                             OCHF.sub.2                                                                            OH                                       726   H     O     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OCH.sub.3                                727   H     O     CH   OCHF.sub.2                                                                             OCH.sub.3                                                                             OH                                       728   H     O     CH                                                                                   ##STR632##                                                                            OCH.sub.3                                                                             OC.sub.2 H.sub.5                         729   H     O     CH                                                                                   ##STR633##                                                                            OCH.sub.3                                                                             OH                                       730   H     O     CH   SCH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                731   H     O     CH   SCH.sub.3                                                                              OCH.sub.3                                                                             OH                                       ______________________________________                                    

                                      TABLE 57                                     __________________________________________________________________________      ##STR634##                                                                                                    Physical nature                                Comp.                           mp (°C.)                                No.  Xn                                                                               W  Z  R.sup.1                                                                               R.sup.2                                                                            R.sup.3                                                                            R.sup.7                                                                            n.sub.D.sup.20                                 __________________________________________________________________________     732  H O  CH OCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           OC.sub.2 H.sub.5                                   733  H O  CH OCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           OH                                                 734  H O  CH Cl     OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                          735  H O  CH Cl     OCH.sub.3                                                                          CH.sub.3                                                                           OH                                                 736  H O  CH                                                                                 ##STR635##                                                                           OCH.sub.3                                                                          CH.sub.3                                                                           OC.sub.2 H.sub.5                                   737  H O  CH                                                                                 ##STR636##                                                                           OCH.sub.3                                                                          CH.sub.3                                                                           OH                                                 738  H O  N  OCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           OC.sub.3 H.sub.7                                   739  H O  N  OCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           OH                                                 740  H O  N  CH.sub.3                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           OC.sub.4 H.sub.9                                   741  H O  N  CH.sub.3                                                                              OCH.sub.3                                                                          CH.sub.3                                                                           OH                                                 742  H O  CH SCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                          743  H O  CH SCH.sub.3                                                                             OCH.sub.3                                                                          CH.sub.3                                                                           OH                                                 __________________________________________________________________________

                                      TABLE 58                                     __________________________________________________________________________      ##STR637##                                                                                                    Physical nature                                Comp.                           mp (°C.)                                No.  Xn    W Z   R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                           R   n.sub.D.sup.20                                 __________________________________________________________________________     744  H     O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OCH.sub.3                                          745  H     O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OH                                                 746  7-F   O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OCH.sub.3                                          747  7-F   O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OH                                                 748                                                                                  ##STR638##                                                                          O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OCH.sub.3                                          749                                                                                  ##STR639##                                                                          O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OH                                                 750  7-CN  O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OCH.sub.3                                          751  7-CN  O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OH                                                 752  7-NO.sub.2                                                                           O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OCH.sub.3                                          753  7-NO.sub.2                                                                           O CH  OCH.sub.3                                                                          OCH.sub.3                                                                          H  OH                                                 __________________________________________________________________________

                  TABLE 59                                                         ______________________________________                                          ##STR640##                                                                                                                 Physical                                                                       nature                            Comp.                                        mp (°C.)                   No.   Xn    W     Z    R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                            R     n.sub.D.sup.20                    ______________________________________                                         754   H     O     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            Cl  OC.sub.2 H.sub.5                                                                     1.5811                            755   H     O     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            Cl  OH                                      756   H     O     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            H   OC.sub.2 H.sub.5                                                                     93-96                             757   H     O     CH   OCH.sub.3                                                                            OCH.sub.3                                                                            H   OH                                      758   H     O     CH   Cl    OCH.sub.3                                                                            Cl  OCH.sub.3                               759   H     O     CH   Cl    OCH.sub.3                                                                            Cl  OH                                      760   H     O     CH   Cl    OCH.sub.3                                                                            H   OCH.sub.3                               761   H     O     CH   Cl    OCH.sub.3                                                                            H   OH                                      ______________________________________                                    

                  TABLE 60                                                         ______________________________________                                          ##STR641##                                                                                                              Physical                             Comp.                                     nature mp                            No.   Xn    W     Z    R.sup.1                                                                               R.sup.2                                                                              R     (°C.) n.sub.D.sup.20          ______________________________________                                         762   H     O     CH   OCH.sub.3                                                                             OCH.sub.3                                                                            OC.sub.2 H.sub.5                                                                     1.5933                               763   H     O     CH   OCH.sub.3                                                                             OCH.sub.3                                                                            OH                                         764   H     O     CH   Cl     OCH.sub.3                                                                            OC.sub.2 H.sub.5                           765   H     O     CH   Cl     OCH.sub.3                                                                            OH                                         766   H     O     CH   OCHF.sub.2                                                                            OCH.sub.3                                                                            OCH.sub.3                                  767   H     O     CH   OCHF.sub.2                                                                            OCH.sub.3                                                                            OH                                         ______________________________________                                    

The herbicide of the present invention comprises a pyrimidine or triazine derivative of the formula (I) as an active ingredient.

For the compound of the present invention to be used as a herbicide, the compound of the present invention may be used by itself. However, it may be used in the form of a formulation such as a dust, a wettable powder, an emulsifiable concentrate, a micro granule or a granule by blending it with a carrier which is commonly used for formulations, a surfactant, a dispersant or an adjuvant.

The carrier to be used for such formulations, may, for example, be a solid carrier such as Zeeklite, talc, bentonite, clay, kaolin, diatomaceous earth, fine silica, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexane or methylnaphthalene.

As the surfactant and dispersant, a metal salt of alkylbenzenesulfonic acid, a metal salt of dinaphthylmethane disulfonic acid, a salt of alcohol sulfuric acid ester, an alkylaryl sulfonate, a lignin sulfonate, a polyoxyethylene glycol ether, a polyoxyethylene alkylaryl ether or a polyoxyethylene sorbitol monoalkylate may, for example, be mentioned.

The adjuvant may, for example, be carboxymethyl cellulose, polyethylene glycol or gum arabic.

In practical use, the herbicide may be diluted to a suitable concentration before application, or may be directly applied.

The herbicide of the present invention may be used for application to foliage, soil or water surface. The blending proportion of the active ingredient is suitably selected as the case requires. However, in a case of a dust or a granule, the proportion of the active ingredient is selected suitably within a range of from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight. In a case of an emulsifiable concentrate or a wettable powder, the proportion is selected suitably within a range of from 1 to 50% by weight, preferably from 5 to 20% by weight.

The dose of the herbicide of the present invention varies depending upon the type of the compound, the weeds to be controlled, the germination tendency, the environmental conditions and the type of the formulation to be used. However, in the case of a dust or a granule which is used by itself, the dose of the active ingredient is selected suitably within a range of from 0.1 g to 10 kg, preferably from 10 g to 5 kg, per 10 ares. In a case of an emulsifiable concentrate or a wettable powder which is used in a liquid state, the dose of the active ingredient is selected suitably within a range of from 0.1 to 100,000 ppm, preferably from 10 to 50,000 ppm.

Further, the compound of the present invention may be used in combination with an insecticide, a fungicide, other herbicide, a plant growth controlling agent, a fertilizer or the like, as the case requires.

Now, the formulation method will be described with reference to typical Formulation Examples. The compounds, types of the additives and blending ratios are not limited to such specific Examples and may be changed within wide ranges. In the following description, "parts" means "parts by weight".

FORMULATION EXAMPLE 1 (Wettable powder)

To 10 parts of Compound No. 625, 0.5 part of Emulgen (registered trade mark of Kao Corporation) 810, 0.5 part of Demol (registered trade mark of Kao Corporation) N, 20 parts of Kunilite (registered trade mark of Kunimine Kogyo K. K.) 201 and 69 parts of Zeeklite (registered trade mark of Zeeklite Co., Ltd) CA were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2 (Wettable powder)

To 10 parts of Compound No. 675, 0.5 part of Emulgen 810, 0.5 part of Demol N, 20 parts of Kunilite 201, 5 parts of Carplex (registered trade mark of Shionogi & Co., Ltd.) 80 and 64 parts of Zeeklite CA were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 3 (Wettable powder)

To 10 parts of Compound No. 42, 0.5 part of Demol N, 0.5 part of Emal (registered trade mark of Kao Atlas K. K.) 10, 20 parts of Kunilite 301, 5 parts of Carplex 80 and 64 parts of calcium carbonate were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 4 (Emulsifiable concentrate)

To 10 parts of Compound No. 453, 80 parts of a mixture comprising equal amounts of xylene and isophorone and 10 parts of a surfactant Sorpol (registered trade mark of Toho Chemical Industries Co., Ltd.) 800A were added, and the mixture was thoroughly stirred to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 5 (Granule)

10 Parts of water was added to 1 part of Compound No. 13, 89 parts of a bulking agent comprising a 1:3 mixture of talc and bentonite, 5 parts of fine silica and 5 parts of a surfactant Sorpol 800A, and the mixture was thoroughly kneaded to obtain a paste, which was extruded through sieve apertures with a diameter of 0.7 mm. The extruded product was dried and then cut into a length of from 0.5 to 1 mm to obtain granules.

Now, the effects of the compounds of the present invention will be described with reference to Test Examples.

TEST EXAMPLE 1 (Test on herbicidal effects by paddy field soil treatment)

In a plastic pot (surface area: 100 cm²) filled with paddy field soil, barnyardgrass (Ec), monochoria (Mo) and bulrush (Sc) were sown after puddling and leveling, and flooded to a water depth of 3 cm. Next day, a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The dose was 400 g of the active ingredient per ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 61. The results are shown in Table 62.

As a comparative agent, benzyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy 2-naphthoate (disclosed in Japanese Unexamined Patent Publication No. 121973/1990: Compound No. 2.5) was used.

                  TABLE 61                                                         ______________________________________                                         Index       Herbicidal effects (growth-controlling                             No.         degree)                                                            ______________________________________                                         5           Herbicidal effect of control:                                                  at least 90%                                                       4           Herbicidal effect:                                                             at least 70% and less than 90%                                     3           Herbicidal effect:                                                             at least 50% and less than 70%                                     2           Herbicidal effect:                                                             at least 30% and less than 50%                                     1           Herbicidal effect:                                                             at least 10 and less than 30%                                      0           Herbicidal effect:                                                             0 to less than 10%                                                 ______________________________________                                    

                  TABLE 62                                                         ______________________________________                                                        Herbicidal effects                                              Compound No.  Ec          Mo     Sc                                            ______________________________________                                          2            3           3      4                                              3            4           2      2                                              13           5           5      5                                             157           5           5      3                                             168           3           5      4                                             437           2           5      5                                             453           5           5      5                                             459           2           5      5                                             622           5           5      5                                             624           5           5      4                                             674           5           5      5                                             675           3           5      4                                             Comparative   1           2      1                                             agent                                                                          ______________________________________                                    

TEST EXAMPLE 2 (Test on herbicidal effects by upland field soil treatment)

In a plastic pot (surface area: 120 cm²) filled with upland field soil, pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 400 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 61. The results are shown in Table 63.

                  TABLE 63                                                         ______________________________________                                                      Herbicidal effects                                                Compound No.   Po    Am         Ch  Ci                                         ______________________________________                                          13            3     4          2   5                                           22            5     3          5   3                                           24            5     5          3   4                                           27            5     4          2   2                                          153            5     2          5   3                                          157            4     5          5   4                                          168            5     5          4   2                                          453            5     5          5   5                                          624            3     5          5   4                                          625            4     5          5   4                                          674            2     5          5   3                                          675            3     5          4   5                                          ______________________________________                                    

TEST EXAMPLE 3 (Test on herbicidal effects by upland field foliage treatment)

In a plastic pot (surface area: 120 cm²) filled with upland field soil, pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil and were cultured in a green house for 2 weeks. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 l/10 ares so as to apply 400 g of the active ingredient per 10 ares. The plants were then cultured in the green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 61. The results are shown in Table 64.

                  TABLE 64                                                         ______________________________________                                                      Herbicidal effects                                                Compound No.   Po    Am         Ch  Ci                                         ______________________________________                                          2             4     5          5   5                                           13            5     5          5   5                                          114            4     3          3   2                                          157            4     5          4   3                                          177            4     5          2   5                                          437            2     5          3   4                                          453            5     5          5   5                                          622            5     3          2   5                                          624            4     4          4   2                                          625            4     5          4   4                                          674            5     4          5   2                                          675            5     5          5   5                                          ______________________________________                                     

We claim:
 1. A compound of the formula (I) or its salt: ##STR642## wherein A is a heterocyclic ring of the formula: ##STR643## wherein R is a hydrogen atom, a hydroxyl group, an imidazolyl group, a C₁ -C₆ alkoxy group, a C₃ -C₆ alkenyloxy group, a C₃ -C₆ alkynyloxy group, a C₁ -C₆ alkylthio group, a C₃ -C₇ cycloalkoxy group, a benzyloxy group, a substituted benzyloxy group, a benzylthio group, a substituted benzylthio group, a C₃ -C₆ cycloalkylthio group, a C₁ -C₄ alkoxy C₁ -C₄ alkoxy group, a furyloxy group, a tetrahydrofuryloxy group, a phenoxy group, a substituted phenoxy group, a C₂ -C₄ aralkyloxy group, a C₁ -C₄ alkylthio C₁ -C₄ alkoxy group, a cyano C₁ -C₄ alkoxy group, a C₁ -C₄ alkoxycarbonyl C₁ -C₄ alkoxy group, an N,N-di C₁ -C₃ alkylamino C₁ -C₃ alkoxy group, an N,N-diC₁ -C₃ alkylamino C₁ -C₃ -alkylthio group, a C₃ -C₉ linear or cyclic alkylidene aminoxy group, a C₁ -C₄ alkylsufonylamino group, a phenylsulfonylamino group, a substituted phenylsulfonylamino group, a trimethylsilylethoxy group, a group of the formula --NR⁴ R⁵ (wherein each of R⁴ and R⁵ which may be the same or different, is a hydrogen atom, a hydroxyl group, a C₁ -C₆ alkyl group, a C₁ -C₆ alkoxy group, a C₃ -C₆ alkenyl group, a phenyl group, a substituted phenyl group, a C₃ -C₆ cycloalkyl group, a C₁ -C₃ alkoxy C₁ -C₃ alkyl group, a C₁ -C₃ acyl group, a C₃ -C₆ alkynyl group, a C₃ -C₅ alkenyloxy group, a C₃ -C₅ alkynyloxy group, a benzyloxy group, a substituted benzyloxy group, a C₁ -C₄ alkoxycarbonyl C₁ -C₃ alkyl group, a C₁ -C₄ alkoxycarbonyl C₁ -C₃ alkoxy group, an amino group, a dimethylamino group, a cyano group, a C₁ -C₄ alkylsulfonyl group, a phenylsulfonyl group, a substituted phenylsulfonyl group, an acetylamino group or an anilino group, or R⁴ and R⁵ may together form a ring which may contain an oxygen atom),each of R¹ and R² which may be the same or different, is a hydrogen atom (provided that a case where R¹ and R² are both hydrogen is excluded), a halogen atom, a C₁ -C₆ alkyl group, a C₁ -C₆ haloalkyl group, a C₁ -C₆ alkoxy group, a C₁ -C₆ haloalkoxy group, a C₁ -C₆ alkylthio group, a phenoxy group, a substituted phenoxy group, a C₁ -C₃ alkoxy C₁ -C₃ alkyl group, a C₃ -C₆ cycloalkyl group, a C₂ -C₅ alkenyl group, a C₃ -C₅ alkenyloxy group, a C₂ -C₄ alkynyl group, a C₃ -C₅ alkynyloxy group, a C₁ -C₃ alkylthio C₁ -C₃ alkyl group, a group of the formula --NR⁶ R⁷ (wherein each of R⁶ and R⁷ which may be the same or different, is a hydrogen atom, a hydroxyl group, a C₁ -C₄ alkyl group, a C₁ -C₄ alkoxy group, a C₂ -C₄ alkenyl group, a C₃ -C₅ alkenyloxy group or a C₃ -C₅ alkynyloxy group, or R⁶ and R⁷ may together form a ring which may contain an oxygen atom), X is a phenyl group, W is an oxygen atom, a sulfur atom or a group of the formula --NR¹⁰ (wherein R¹⁰ is a hydrogen atom, a C₁ -C₃ alkyl group, a C₂ -C₅ alkenyl group, a C₂ -C₄ alkynyl group, a C₁ -C₃ alkoxy C₁ -C₃ alkyl group, a C₁ -C₃ alkylsulfonyl group, a phenylsulfonyl group, a substituted phenylsulfonyl group, a C₁ -C₃ acyl group, a benzoyl group or a substituted benzoyl group), Z is a methine group, and n is an integer of from 1 to
 2. 2. A compound according to claim 1, wherein W is oxygen, R¹ and R² each are methoxy, R is OH and n is
 1. 3. A herbicide containing a compound as defined in any one of claim 2, as a herbicidally active ingredient. 